Please enjoy this transcript of my interview with Harley Finkelstein (@harleyf), an entrepreneur, lawyer, and the President of Shopify. He founded his first company at age 17 while a student at McGill. Harley is an advisor to Felicis Ventures, and he is one of the “dragons” on CBC’s Next Gen Den. In 2017, he received the Canadian Angel Investor of the Year award and Canada’s Top 40 Under 40 award, and in 2016 he was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the board of the C100, and from 2017 to 2020 he was on to the board of directors of the Canadian Broadcasting Corporation (CBC).
Transcripts may contain a few typos. With some episodes lasting 2+ hours, it can be difficult to catch minor errors.
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This interview was transcribed by Rev.com.
Tim Ferriss: Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode of the Tim Ferriss Show where it is my job to deconstruct world-class performers of all different types, to tease out the habits, routines, favorite books, and so on that you can use, cereal maybe, who knows, morning routines.
My guest today is Harley Finkelstein. On Twitter @HarleyF. Harley is an entrepreneur, lawyer, and the Chief Operating Officer, that’s COO, of Shopify. He founded his first company at age 17 while a student at McGill. Harley is an advisor to Felicis Ventures and he is one of the dragons on CBC’s Next Gen Den.
In 2017, he received the Canadian Angel Investor of the year award and Canada’s Top 40 Under 40 award. And in 2016, he was inducted into the Order of Ottawa. From 2014 to 2017 Harley was on the board of the C100. And from 2017 to 2020 he was on the board of directors of the Canadian Broadcasting Company, CBC in other words. Twitter @HarleyF, Instagram @Harley. Harley, welcome to the show.
Harley Finkelstein: Hey, Tim. Thanks for having me. It’s a real honor to be on the show.
Tim Ferriss: I love interviewing my friends because it gives me an excuse to do a deep dive and interrogate in a way that would just be totally abnormal and maybe sociopathic over a dinner table. And I thought we would start with describing or explaining what Shopify is for those who may not know.
Harley Finkelstein: It’s interesting. I mean, Shopify has obviously grown considerably over the last couple of years certainly post IPO in 2015, people read about us more often. But I think most people know us as an ecommerce provider, an ecommerce 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.
Tim Ferriss: And if we wanted to peg some numbers to that, any kind of stats or numbers, what can you share that would give people maybe an infographic of the mind, an ideal of the scale and scope of what we’re talking about?
Harley Finkelstein: So we currently have over a million stores on Shopify, so a million businesses, a million brands host their commerce on Shopify. The majority of those brands would self-identify as small businesses and some of them that were small grew into be really, really big businesses, the Allbirds of the world or the Bombases of the world, or the Gymsharks of the world or the Fashion Novas. But for the most part we have a million stores on the platform. And if you were to pretend for a second, we’re not a retailer but if you were to pretend just for a moment that Shopify was a retailer, we would be the second-largest online retailer in America after Amazon.
And the reason I mention that is because one of the things that has happened over the last couple of years as we’ve grown and have become, for a lot of people, the default commerce platform, we’ve been able to aggregate a ton of the stores to get economies of scale, which we then give to entrepreneurs and help level the playing field. And you and I have spent countless hours talking about what it means to level the playing field for entrepreneurs. And in terms of the company, it depends on the day you look we’re a publicly-traded company, our market cap is above a hundred billion which still sounds unbelievable to say and something that is amazing. We have about 6,000 employees across 17 offices all over the world and in Q2 of this year, so this past quarter, we’re talking 2020, our merchants sold about $30 billion worth of products on Shopify. So, that’s some of the high-level stuff.
Tim Ferriss: All right. So, we’re going to stay on the present tense for a little bit, and then we’re going to zoom past tense. Present tense, or I suppose this encapsulates any period of time really but what books have been most formative for you in your business journey with Shopify and/or what have you gifted the most to other people, what books?
Harley Finkelstein: One of the books that was suggested to me early on in my Shopify journey was High Output Management, which is the Andrew Grove book, who had obviously built Intel and had done an amazing job. And one of the reasons that it was recommended to me was it seemed to cut through a lot of the BS of most business books. For better or for worse I went to business school and we can talk about education stuff. I actually found law school to be 10X more valuable and instrumental for my journey as an entrepreneur in running a big company but I did go to business school. The business books that they naturally give out I thought were full of platitudes and full of things that I just didn’t find very wise. Whereas I found High Output Management to be by far one of the greatest books. And then actually I think Ben Horowitz’s book The Hard Thing About Hard Things is almost like a modern iteration of High Output Management as well. And that’s been another big part of things that have been valuable to me in my own career.
That said, we are in the middle of a global pandemic, and one book that I recently re-read that I know that you know about is Taleb’s book Antifragile. And the reason I’ve found it incredibly valuable to reread it is it feels like we’re in a time of great breakage, of great change. And it feels to me like what is emerging through this global pandemic are two types of people and two types of entrepreneurs and two types of individuals which is those that are resistant that are waiting for things to go back to the status quo that are looking forward and anticipating when normalcy will return. But then there’s this whole other cohort of people, a whole other cohort of businesses even, who are resilient, who are not waiting for the status quo to return but rather are thinking about how they can use what is happening as this incredible catalyst to change everything and to pivot and to adapt.
And the neat part about Antifragile is it talks about obviously the two main systems being robustness and fragility, but then Taleb introduces 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 two people in the same circumstances and one just resist and the other simply is resilient about it and that book just encompasses that.
In terms of the book that I’m reading right now is I’m actually reading, this a shocking but I’m reading my first fiction book ever. I’ve never read fiction in my whole life, I just wasn’t into it. And I know it sounds so crazy but 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 a generally fascinating book about an interesting, true story. And I’m actually reading The Alchemist right now and I know that’s a book you know well. And it’s amazing because the relationship that I have with reading The Alchemist relative to reading a book that where I’m highlighting, I’m trying to digest, I’m trying to reflect on it, is just completely different and it’s actually a lot more enjoyable.
Actually, one of the books that I’ve given out the most, it’s probably not the book but in the early days of Shopify I probably gave out 100 copies of The 4-Hour Work Week. And I’m not saying that to flatter you and we’re 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 that you’re doing whether you’re in school or you have another job that was somewhat foreign. And yet I knew that if we encouraged more people to experiment with side hustles it would lead to entrepreneurship and hopefully it would eventually lead to them using Shopify. So certainly that was an important book in my life but also in Shopify’s life.
Tim Ferriss: 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 been projected for 2030 have been pushed to the front of the line of very, very quickly so things have been compressed. So I want to ask you about the future of retail but before we do I want to talk about the past of Shopify and I thought maybe a useful way to frame that or just a fun way to frame that would be number one can you repeat the number of employees and market cap of the company right now depending on the day obviously, but give or take?
Harley Finkelstein: About 6,000, I think we’re over 6,000 employees and market cap is a hundred and something billion depending on the day. I think it’s around $120 or $130 billion.
Tim Ferriss: And when we first met, how many employees were there and what was the market cap, so to speak?
Harley Finkelstein: We first met in mid-2010. We had probably around a dozen people at the company in total. And I think we had just, either had just raised or about to raise our series A.
Tim Ferriss: Just about to raise.
Harley Finkelstein: I think we were just about to raise our Series A and I think our Series A was, I mean it was sub $50 million, I don’t remember the exact number but it was definitely sub $50 million. So, I guess a lot has changed from our original encounter Tim to now. And wow yeah I think when you put it in that perspective with that type of delta it does seem quite incredible.
Tim Ferriss: And so I think this is a good time to just say, and of course I’ve said this before, and you and I have shared a lot of tacos and not a small quantity of tequila on occasion, but I just want to say publicly that it has been such a joy to see you and your family and obviously your close friends like Tobi 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 comes from. But not losing my train of thought it couldn’t have happened to just a nicer group of people. I really feel that way and I just want to congratulate you. It’s been awesome to watch in the very literal sense of awesome so well done.
Harley Finkelstein: I appreciate you saying that. It’s been the journey of a lifetime and there is not a second that goes by that I take any of it for granted. I think that part of the story is that we’ve built something special and meaningful and valuable to the world but also we’ve done it — Tobi 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 community, people they spend the most amount of time with but there’s also 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 founders going back a 100 years at some point there is this natural graduation where someone decides it’s time to bring in the “adult supervision” or something like that and you lose the connection with the founding story. But because for the most part, those of us that are still at Shopify today are still the same group that were there in the early days we’ve brought each other along with us, and we’ve brought our friends along with us also and it’s made for a much richer experience. It’s made for a much more meaningful journey when you do it with people and you grow together.
Now, obviously, the flip side of that is in order to do that every single person, particularly on the leadership team, has to requalify for their job every single year. And that is difficult in year one and year two, it becomes incredibly difficult in year 10, year 11, and year 15, where the stakes, the challenges, the opportunities are all so much bigger. But I think for the most part we’ve all focused on requalifying for our job and also keeping our I don’t want to say modesty but just staying grounded in this whole thing and realizing that we’re the same folks who were there at the beginning. And in that way, it’s just been a really awesome experience for us.
Tim Ferriss: Well, you guys are still nice Canadian boys.
Harley Finkelstein: Maybe it’s a Canadian thing, maybe the only reason we’re nice is because we’re Canadian. And I can tell you that there are some challenges that come with the Canadian thing as well. There’s a lot of great advantages. There’s something called the tall poppy syndrome here in Canada, which is you don’t want to grow too tall because someone’s going to chop you down. And you do feel that from time to time but for the most part building a company outside, a tech company outside of Silicon Valley I think has been incredibly valuable to us.
Tim Ferriss: 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 of one of the largest tech companies in the world for instance. And then I’m going to bookmark tall poppy syndrome, we will probably not come back to that so it’s more of a note for myself, but I didn’t realize it was an issue in Canada as well. It’s an issue throughout the entire Commonwealth. 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 requalifying for the job, we’re going to come back to what that means. And I’m going to go further back to law school, you said something about law school. Now, I’m going to get the pronunciation incorrect possibly. Philip Rimer, is that his name?
Harley Finkelstein: Wow. You’ve done your research, Jesus.
Tim Ferriss: I have, I’ve got a full dossier. I’ve got a full dossier. So who is Phillip Rimer and why is he relevant?
Harley Finkelstein: Yeah, so I was born in Montreal in Canada, lived here until I was 13. When I was 13 there was a referendum in Canada, in Quebec where I lived, where Quebec as a province wanted to separate from Canada. And the referendum never actually went, 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 —
Tim Ferriss: Can I pause you for a second?
Harley Finkelstein: Sure, absolutely.
Tim Ferriss: I actually didn’t know this piece of the puzzle. How on earth do you choose South Florida?
Harley Finkelstein: If you’ve ever been to Montreal, it’s the most amazing city in the world. It feels European almost but it’s in Canada which is a wonderful country but it’s cold as hell. And Februarys in Montreal are notoriously bad because it gets dark very, very early, the number of sunlight hours is very small. And it’s not just February, I mean it’s basically January until the end of March. And I think my parents as they were deciding where they possibly could move to I think it was going to be somewhere warm. And so it was a combination of staying on the east coast, EST time zone, and the fact that we had some friends and family that had been living there already. And so, they just decided, “Let’s go somewhere hot.”
And so yeah, we moved down and this is probably 1996, moved down to South Florida. And then after high school, it was time for me to consider where to go to college. And my parents didn’t have very much money and so if I were to go to a US school, it would have required me to take out some sort of student debt. But because I was born in Montreal, McGill University, which is a great school, had offered basically me in-state tuition and it was like $1,800 a year. And I loved Montreal, McGill was a great school, and it was $1,800 a year. And so my parents were like, “You’ve got to go to McGill.” I get to McGill in September 2001 and 11 days later September 11th happens, stock market crashes, things get really, really bad and my parents lose everything. I mean, we lost our house, we lost everything. We didn’t have a penny to our name.
Tim Ferriss: Why is that? That’s because of the equity markets?
Harley Finkelstein: My dad was just over-leveraged for the most part. He was doing things he probably shouldn’t have been doing. And he just did stuff that was just highly correlated to the equity markets doing well, and when the equity markets fell apart things fell apart for us. And my mom called me and said, “Hey, you’ve got to move back down to Florida because there’s no way you can stay in Montreal. We can’t give you money. Just come back down here and we’ll figure it all out.” And I was 17 years old when I started McGill, I was a bit younger than my peers.
I loved Montreal, I 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 going to also try if I can to help the family out as well.” I have two much older sisters, so I thought, “Okay, I’ll figure this out on my own.” And I tried my hand at a bunch of stuff. I worked at a travel agency. I’ve been a DJ since I was a kid, so I deejayed parties and events and weddings and anything that —
Tim Ferriss: And bar mitzvahs.
Harley Finkelstein: And lots and lots of bar mitzvahs, like 300 bar mitzvahs as you know, we’ve talked about that a lot. And so, I deejayed, 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 can still have a full-time classload 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 interesting is that McGill University spends $25,000 every semester on promotional t-shirts, the stuff that you see in the bookstore, the stuff you get in your orientation bag that says “faculty of science” or “faculty of arts” or whatever it is. Hey, if you want to start something, that might be an interesting thing to start.”
And Montreal has historically had this incredible, they call it the schmatta business but it’s basically the apparel industry. You have companies like Buffalo and American Apparel and Paris Sukkot and countless other companies have all been created from Montreal. There’s a very well known, well-developed clothing, business, and clothing industry. And I thought, “Okay, cool. Well, let me just…”
Tim Ferriss: What was the colloquial name for it?
Harley Finkelstein: Schmatta business.
Tim Ferriss: Is that Yiddish?
Harley Finkelstein: Yeah, it’s a Yiddish term that basically means clothing. And part of it was Montreal was an absolute immigrant town. My family came to Montreal from Hungary in ’56. But it’s an immigrant city and so the neat part about the apparel industry or the schmatta business was that it had a low barrier to entry, so you can start a business with little capital. And I had little capital but I have 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 two to four years, I guess two years until it took off but four years in total selling t-shirts all through undergrad to almost every university across Canada.
Tim Ferriss: So it worked?
Harley Finkelstein: Well, it worked to some extent. It worked that it allowed me to pay my tuition, it allowed me to help my mom and my dad and my siblings. It helped sustain me so I can finish undergrad and not have to move to part-time classes. What it didn’t do though, and this is where Phil Rimer enters the picture, one thing that has been really valuable to me growing up was I was always able to have this group of mentors in my life. And I know you talk a lot about mentors and we’ve talked a lot of mentorship but I’ve always had these groups of people in my life who I just really admire for totally different reasons and I’ve taken this pretty far.
Lindsay and I got married in 2013. Basically six months prior to getting married, there were three people that just seemed to have the greatest relationship to their spouse, and I called them and said, “Hey, tell me about being a great spouse.” I did the same thing for being a dad, I did the same thing in a bunch of different aspects of my life. But when I was starting out in entrepreneurship at McGill, one of the people that I contacted was this guy, Phil Rimer, 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 it in just this very simplistic, digestible way.
And so, like I did throughout my undergrad years I called Phil towards the end of my undergrad and said, “I have this little business, it does well, I think I’m just going to continue building this business.” And his insight was, “In the same way that you were able to disrupt a bunch of existing incumbents selling university’s 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 have that connection with them.” But that was it.
And his proposal or his idea was: “Have you thought about going to law school?” And I was like, “No, I don’t want to be a lawyer. Why in the heck would I go to law school?” Anyways what he did was he said, “Look, next year I’m teaching law at the University of Ottawa.” And I mean he’s doing it part-time, he’s 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.”
Tim Ferriss: The Downton Abbey of entrepreneurship.
Harley Finkelstein: Yeah that it would teach you how to write, how to think critically, how to debate, how to argue. It would teach you how to read 4,000 pages and pick out the one line, they call it the ratio decidendi, the one line that matters in any court case. You’ll be able to pick that out of 4,000 pages. And he convinced me that that actually would be an incredible advantage in my career to become an entrepreneur. And so, I applied to one law school on the advice of this guy, Phil Rimer, and I got in at the University of Ottawa, and I moved here in 2005.
Tim Ferriss: Now you, I suppose, hinted at what you gained from your law education. What would you say — you mentioned a few things that he speculated you would learn. Were the most valuable things you learned those? Were they other capabilities or skillsets? What were the main things you took away from that? And I should say also as a side note that many, many successful entrepreneurs have law degrees but didn’t practice law, Peter Thiel, Chris Sacca both billionaires who have been on the podcast among them. So, that is one common thread that shows up now and again. But what were the most valuable things in retrospect that you gained from that experience?
Harley Finkelstein: Are you familiar with the Socratic method? Do you know that term?
Tim Ferriss: I do have some familiarity with the Socratic method, but if you could explain it if that’s going to be part of the answer.
Harley Finkelstein: You’ve studied Socrates and some of his work so I assume there’s origins there, but law school uses the Socratic method, which at least the iteration of it in the law school that I went to was they would ask, the professor at the front of the class would ask a question and would randomly call out somebody’s name. And if you answered it correctly you did well and if you didn’t answer it correctly or you weren’t present you would do poorly. Attendance mattered which was very different than my undergrad. And one of the things that, this is such a strange takeaway from law school, but the Socratic method made me really, really good at thinking on my toes. It forced me to [understand] that you couldn’t read every single piece of assigned work because, by the nature of law school, a lot of the intention is to overwhelm you with content and readings and work so that one, you can get ready for the practice of law in the corporate world I suppose, but also, they wanted you to be able to start making good decisions about how to acquire information in the most effective way.
The Socratic method for me was incredibly valuable because it meant that if I was given three cases to read, and one of the cases was 1,200 pages and I can’t read that in 24 hours, I would have to understand how to get the information, how to acquire the information in such a way that I could regurgitate it or I could repeat it if I was called on. But not know enough about it that if I didn’t get called on it it would prevent me from doing well in another class who also used the Socratic method. And that ability to quickly stay on my toes and be ready at any moment to answer a question in a way that provides the professor with the information or to substantiate that I know what I’m talking about but didn’t necessarily require me to spend all of my time perpetually studying, that actually was one of the most valuable things.
So I would say that in the second thing is writing. In Montreal I went to a Jewish private school and in the States I went to a very large public high school and it was a really good public high school. But I got to school, I went to McGill for undergrad and I had never really learned how to write really well. And I only realized that in law school. I only realized in law school that I was able to write a lot but it took me a long time just to get to the point.
And that actually was another major piece of, it was shaped as a pedagogical learning but it wasn’t actually pedagogical, it was super practical that it taught me how to very quickly reply and quickly think on my feet or on my toes but it also taught me how to write really, really well. And for those things alone, I wouldn’t change it for anything in the world. Which is very, very different than — I don’t want to slam MBAs, but I did a joint law MBA so I also went to business school. Whereas the MBA was entirely case-study based most of the case studies I felt were not even steeped in any type of reality. I did not find that to be at all valuable relative to my law degree to run a company like Shopify today.
Tim Ferriss: So I want to follow up on the Socratic method or acquiring the information that you need without digesting the 1,200-word tome. There are different aspects of 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, they’re very fun, very opinionated. So you have Wittgenstein in 90 Minutes, Plato in 90 Minutes, and I think there are somewhere between 10 and 20 of these volumes and they’re very quick to digest as the titles would imply. But I’m going to read just briefly for folks a description of dialectic from Wikipedia, and here’s what it says. “The Socratic dialogues are a particular form of dialectic known as the method of” — and here you can probably correct my pronunciation, but “elenchus,” E-L-E-N-C-H-U-S; I don’t know if that is from Latin or elsewhere — “(literally, ‘refutation, scrutiny’) whereby a series of questions clarifies a more precise statement of a vague belief, logical consequences of that statement are explored, and a contradiction is discovered.”
So this is I think a different aspect than what you’re talking about. So I’d love to hear you perhaps give an example of how you would tackle fixing that impossibility of reading the 1,200 pages, what approach you might take. But I want to point out for people listening also if they haven’t done any type of debate, which by the way is something that if you ever see Peter Thiel on stage, you will realize he has a lot of training, 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 and so you can effectively in the realm of debate lead someone to defeat themselves before you ever take a counter position, if that makes any sense
Harley Finkelstein: 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 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 that the teacher would ask a question randomly to a student and say, “Mr. Finkelstein, tell us about this particular case.” And then what he or she would do is they would ask question after question which helped them substantiate whether or not I understood the case itself.
So for example, “Hey, what’s this case about?” I would say, “Well, this is a tort case for example and someone fell on someone else’s property.” “Okay well, why is this controversial?” “Well, the reason is the property that they fell on wasn’t actually the homeowner’s property it was city property.” “Well, okay.” And I always tried to 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 fault, it’s not even about the tort itself, it’s about some other thing that the professor believes will be valuable for these students to go off with after this.” And usually it’s something that is far more universal and far-reaching than just, “Well, this is how the case ended.”
And so, what I tried to do constantly was, okay this case X versus Y here fundamentally the professor wants to get to the point where we can have a discussion about city land. And so, how do I go from the overview of the case to discussion with city land and through that questioning and through that critical reasoning and critical debate? I was able to draw some sort of almost literally a map between that initial question to the final question. If I was able to get that, none of the other details really mattered. The problem was not all teachers were consistent in that way and some professors didn’t actually think critically about what the lesson was, not all professors are at the same level. Some are bad professors, frankly. At every school, not everyone’s going to be the greatest professor of law at every single school. And so I’d figure it 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.
Tim Ferriss: 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.
Harley Finkelstein: I need to research this because I forgot the name of the book. I think it’s called The Elements of Style. There’s a book called The Elements of Style, I think that’s what the book is called here.
Tim Ferriss: Yes. Strunk and White?
Harley Finkelstein: Yeah, exactly. That’s right, Strunk and White. Frankly, everything I learnt in law school from a writing perspective, The Elements of Style would have taught me already. I think it was written in the 1920s. Yeah, 1923.
Tim Ferriss: Very short book.
Harley Finkelstein: I think it’s 60 pages or something.
Tim Ferriss: 43 pages.
Harley Finkelstein: 43 pages.
Tim Ferriss: Published in 1918.
Harley Finkelstein: Wow. Yeah. If I didn’t go to law school, but I want to replicate some of those learnings, some of those lessons, The Elements of Style was a big one. That would be first. The second thing that actually it did was, we had a lot of guest lecturers in law school and I went to law school in 2005, YouTube was probably around. It wasn’t necessarily as popular as it was now, but one of the things that the professors did, and I think a lot of law schools do have this type of dynamic where they bring in guest lecturers. When you bring in someone, this is why I love podcasts so much, or interviews for that matter so much is because, when you bring in someone who’s written a book and you give an hour of their time and you ask questions about the book, you tend to very quickly get to the part of the book that they loved writing the most. Not always, but that tends to be the major takeaway.
And if there’s 12 chapters, usually the writer or the author in this case, legal textbooks, the legal scholar on the topic will very quickly get to, “Okay, 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 podcasts and great interviews and just really high-quality conversation. And probably the third thing is, you had sort of said this earlier, but we did moot court, M-O-O-T, which is effectively like debates. You’re pretending like you’re in court. There’s a judge, there’s a jury. There’s two sides of a particular argument and whether it’s debate or it’s moot court that has been instrumental in my life. I loved moot court. I did quite well. I was able to compete with other schools and people in different countries. 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’s he or she is looking to prove that you’re wrong. Man, I think that is incredibly instrumental.
Tim Ferriss: Yeah, for sure. To build on a few things you said, along with The Elements of Style, there’s a great book called On Writing Well, by William Zinsser. Z-I-N-S-S-E-R, it’s a classic. It’s a bit longer, 300 and some odd pages, but I found it incredibly helpful for removing ambiguity and what one might call in the legal profession, puffery, maybe not in Canada. But in the US.
Harley Finkelstein: Yes. No, totally.
Tim Ferriss: I’ll give an example. If you have ever bought a shampoo that says “increase vitality” or “hair volumizer,” these are words that have no meaning. They can’t have a meaning because that would then be a structure or function claim. And it would require all sorts of other regulatory hurdles for an over the counter product like that. Or “toning,” in the realm of exercise, that does not have any physiological meaning whatsoever.
And to help clean up, declutter your mind of these types of words or any type of bloat, these types of books are super helpful. Furthermore, one thing you can do, and I’ve done this before with my own writing is to ask friends or to hire someone like a star law student, they don’t have to be a lawyer, to edit your writing. And they could be arbitrary writing assignments, it doesn’t matter. Make it an assignment for yourself, if you have the budget or the access, or the ability. Three pages a week, you have a three-page assignment every week and you have someone with legal training, go through it, to redline the shit out of it because they will identify anything that were in a contract, let’s just say, would immediately get spotted by one side or the other, because it’s unclear. And if you need something to be defensible or to withstand scrutiny of the court, you’ve got to ferret that shit out right away. And it’s super helpful.
Harley Finkelstein: It’s funny. I’m just reading, Stephen King wrote a review of Elements of Style. And this is a funny review that he’d wrote. He said, “There is little or no detectable bullshit in that book. (Of course, its short; at 85 pages, it’s much shorter than this one.) I’ll tell you right now that every aspiring writer should read The Elements of Style. Rule 17 in the chapter titled Principles of Composition is ‘Omit needless words.’ I will try to do that here.” That’s his entire review of the book.
Tim Ferriss: Yeah. I have another one next to me, just for nerds who want to really go crazy. Literally a book that I have with me today called Draft No. 4: On the Writing Process by John McPhee, M-C-P-H-E-E on the writing process, which if you really are a nerd and want to study structuring, how you structure a piece, that’s a really excellent book as well.
Harley Finkelstein: Awesome. Yeah.
Tim Ferriss: Before we move on from books real quick, you mentioned The Alchemist, Paulo Coelho. Two things on that. Number one, for people who don’t realize, yes, that book has sold something like a hundred million-plus copies in many languages. It was a complete failure in the beginning. It was rejected, it was pulled from circulation. And Paulo has been on the podcast. I want to make one fiction recommendation to you, and that is Dune by Frank Herbert. And I think it will go right up there next to the Horowitz book and next to Andy Grove in terms of maybe not management, but leadership books. I think you’ll be very impressed with it. Let’s come back to your job. What do you do at Shopify, Harley?
Harley Finkelstein: My official title is Chief Operating Officer. And from a sort of divide the world and conquer perspective, I look after more of the business side of Shopify, the commercial side of the business. But actually, we talked a bit earlier, but this idea of requalifying for your job. Part of that annual requalification that I’m trying to do each and every year is to also understand how to add the most amount of value. And one of the things that I think is really important in the early days of any company, and actually it’s super important as a company ages, but certainly in the early days where you don’t have 6,000 people, is to figure out, okay, what are the ways I can add value. Things that only I can do, things that have the greatest impact, things that I enjoy doing.
And the one common thread or common theme, I’ve been at Shopify for more than a decade and I’m 35. Almost a third of my life I’ve spent at Shopify, which is 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 about Build a Business because probably the first real storytelling opportunity that we did as a company was Build a Business, and you were the co-founder of Build a Business; we can get to that later. But I would say today, my job is, besides the storytelling thing, it’s bringing on some of the brightest, sharpest humans on the planet to Shopify and then making sure they absolutely have no roadblocks or constraints in their way so that they can do their life’s work with us together. That sounds a little bit Mother Goosey, but that’s truly how I spend my time.
Tim Ferriss: That’s a great adjective. I am going to use Mother Goosey in the future. Storytelling is important, persuading is important. That’s another skill you were able to practice in law school. And that applies in the Build a Business competition, which we’ll get to, also applies in fundraising. Also applies in perhaps telling your own story to other people you meet along the way and let’s go way back. And I would love to hear you describe how you first met Tobi. Who is Tobi? How did you guys first meet and how did you become involved with this whole shebang?
Harley Finkelstein: I mentioned earlier, 2005, I moved to Ottawa on the advice 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 between Montreal and Toronto, which are two of the major cities in Canada. I arrived here and starting law school and I have no friends, I have no family here. One of the things that was really valuable to me in Montreal when I was going to McGill was my tribe. The people that were sort of my people, my community, people that I hung out with, were also entrepreneurs. And that happened sort of organically that I just met other entrepreneurs and we became really good friends. And it just worked.
And I began to believe that in order for me to find my new tribe, my new group of people in Ottawa, I needed to figure out where the entrepreneurs were. And I just called a bunch of random business incubator type organizations, one was called Invest Ottawa. And I just asked around where the entrepreneurs hung out. And someone said there was a group of entrepreneurs that hang out every Friday night in this coffee shop in Ottawa called Bridgehead.
Tim Ferriss: Like the Parisian poets.
Harley Finkelstein: I guess, yeah. It’s far less sophisticated than that and certainly far less glamorous. But I was told that these guys hang out at this coffee shop. And I walk into this coffee shop and it was a group of five or six people. And some of these people, it was Luc Levesque, who created TravelPod, who then went and built Messenger Kids at Facebook, he actually just recently joined Shopify. There was Sam Zaid from Getaround, which is a San Francisco startup. Aydin Mirzaee, who did FluidSurveys, he’s now doing Fellow. And it was Tobi, and Tobi was an immigrant to Canada. He’d moved here a couple years prior to that from Germany. He moved here because of Fiona, he met a girl who’s now his wife and he moved to Canada. And he initially, because he couldn’t work, he couldn’t get a job. Someone told him that without having your social insurance number in Canada, you couldn’t get a job, but you could start a business. 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 he sought out to try to sell snowboards on the internet and built a company called Snowdevil. And at the time, this is like 2004, there were two ways to sell something on the internet. The first way was, you paid a million dollars to some sort of enterprisey type of company, Oracle or IBM or SAP, or just these big enterprise companies. And they would do this big, massive insulation for you for ecommerce, but it was really expensive. On the other side, you could use and sell yourself 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’re renting customers from that marketplace. You never actually own your own set of customers. And so Tobi being Tobi, and being this incredible software product genius, and I say that — you know him, so you know that that’s completely accurate.
Tim Ferriss: Yeah, that’s not an exaggeration.
Harley Finkelstein: That’s not an exaggeration at all. He didn’t like those two options. And so we created a third option and he wrote this piece of software. He was using a new coding language at the time that was incredibly contemporary called Ruby on Rails. He was one of the core members of Ruby on Rails. And he wrote this piece of software to sell these snowboards. And he had a really good snowboard business, Snowdevil. it was a really cool business, but eventually as the summer came and people were not buying snowbirds anymore, he had a decision to make. Either he would start selling skateboards or something for the summer, surfboards, or he would take the thing that he had built for Snowdevil and allow other people to use it to build their own online stores.
And he decided to do the latter and focus on the software side. The snowboards were a good idea, but he really believed the software side of it was a great idea. And he created Shopify and this idea was anyone that had a product to sell was able to use Shopify and very easily set up a beautiful online store. And I was one of the first people that used Shopify. I met him at this coffee shop. I told him that I was looking to move my t-shirt business from a wholesale promotional business, which required face-to-face engagement into more of a virtual business that would run while I was sitting in tax law and in my classes in law school. And I became store 136, I built a little store called Smofer. S-M-O-F-E-R. Yep. That’s true.
Tim Ferriss: What the hell is smofing?
Harley Finkelstein: This was sort of the time Zappos and Google and a lot of the company names of that vintage were made up words, the next iteration was the ify vintage and the next iteration was the .io vintage. But this vintage, when I started, it was just a lot about finding random words and the URLs and .coms were available. I started this little t-shirt business called Smofer. It was a licensed t-shirt business, so I own the rights to some of the Marvel comics and DC comics and some of the rock bands licensing and just started selling these t-shirts on Shopify. And more importantly, or equally as important, the same time I really started to develop this wonderful friendship with Tobi.
You know us both really well. He and I are polar opposites in most ways. He is cerebral, I am incredibly extroverted, he’s a little bit less extroverted. I know you’ve referred to me as a power extrovert.
Tim Ferriss: A little bit less extroverted.
Harley Finkelstein: Significantly less extroverted than me. The way that he sees the world is very different than I see the world. And in many ways, we really connected on a mutual admiration and mutual love of entrepreneurship and company building and commerce, but we also enjoyed the differences of each other. When I was first setting up Smofer, I wanted him to waive the fees because he was a friend of mine and I thought he should waive the fees for Shopify. And so I would basically call him every single week and ask him to waive the fees. And I think eventually, he got so annoyed that he just made my store completely free. And years later of course, when I decided to join, he would say that I was this monster, and he made me his monster; I’m supposed to sort of be on the outside. But we became really good friends.
Throughout law school and business school, I was a Shopify merchant. I fell in love with Shopify. I thought, how incredibly democratizing is it that me, I was probably 22 years old at the time, some punk kid. I didn’t have that much money, I had enough that I was able to start a store, but not enough that I was able to do anything meaningful, that I was able to build a beautiful business while sitting in tax law class that was able to compete against the largest companies on the planet. The other folks that had the Batman Dark Knight license was Walmart in Canada. Literally, I was sitting in tax law class as a complete nobody and I was competing against one of the largest companies in the world. And I was only able to do it because of this piece of software. This software was just magic to me.
Tim Ferriss: Let me hit pause for a quick second. We’re going to come back to the magic of the software. I want to talk about how the hell you got the licensing agreement if you’re selling faculty of law, faculty of this, that, and the other thing t-shirts how did you go about getting the other license aside from Walmart to sell these?
Harley Finkelstein: The licensing world is really interesting because what happens is you have what’s called a master licensor 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, yeah, like a legacy deal. Someone acquired the licenses a long time ago and has held onto it. But then you have these things called sublicenses. And what was neat about that was, there was no way that I was able to afford the license for any of these t-shirts or any of these logos in Toronto or Vancouver or Montreal. They were just too big of a city and they were too expensive, but there were all these, not even secondary cities, these tertiary cities or tertiary regions where no one had the license for it, and no one really wanted the license for it.
And my thinking at the time was, one of the shirts that did really well was when the Batman Dark Knight movie first came out. I think it’s around 2006 or 2007 at this time. I knew that I was able to acquire, for a limited period of time, the license for The Dark Knight Batman logo, which was the new franchise, it 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. what I tried to do is, I tried to find cities where there was a movie theater, but there was no shopping mall. And 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 Night 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 was still fairly new and it would result in them eventually coming to my online store. I did not have the rights to sell this in any major city and frankly, any city with more than 100,000 people. But I had lots of small areas, geographies across Canada, where I was able to sell it to a very small demographic. It only lasted, I don’t know, two years or so before some big company came and bought all of these licenses and I wasn’t able to sell it anyway, but that’s 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 recognizes the value to it because they’re using a physical retail business case or business model for it. But if actually, if I’m selling it online, then who cares where they’re based? And that’s how it happened.
Tim Ferriss: That’s amazing. When did you, or I should say rather how, when is also pertinent, but how did you end up joining Shopify? What was the conversation or the email? What was the actual process?
Harley Finkelstein: Now you’re winding me up. After grad school, I moved to Toronto. 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 to be a lawyer, you have to do this thing called articles, which is a 10-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 10 months, you write the bar exam and you get called to the bar and then you’re a lawyer. And that’s all, that process is finished.
I moved to Toronto in 2008, to article at a fairly large law firm in Toronto. And for the first time in my entire life, Tim, I realized what people were talking about when they were using expressions like “a case of the Mondays” or “TGIF,” or “living for the weekend,” that my entire life my relationship with work, whether it was deejaying or selling t-shirts or it was 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 loved working. I found it very satisfying and I’d like the challenges of it. I’d like 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 a bit legacy.
They wanted to know who I knew. They wanted to know how many years I’d been there. Because I was a first-year lawyer, I was being given work that was appropriate for a first-year lawyer, as opposed to being given work based on my capacity. I was told to do things in a certain way because that is what articling students do. And because I was a first-year lawyer, because I didn’t come from some fancy last name family, I didn’t necessarily understand how to do well in that environment. In fact, it completely depressed me. I didn’t like what work was becoming for me. My Sunday nights were the worst period of the week. I would get this knot in my stomach.
And what I loved about entrepreneurship was my Sunday nights always felt like my Friday nights. And I loved that about it, that Saturday morning or Monday morning, it all feels the same. Probably halfway into the articles, month five or six of working at this law firm, I called Tobi and said, I really want to join you. And at the time it was Cody and Daniel as well. And I really want to join you guys and help you build something big and meaningful and important. And it was mostly Tobi, Daniel, and Cody are three of the most brilliant humans I’ve ever met. They’re certainly on the technology side and the R and D side. And I felt I can come in and help on the business side. And that was that first call. And I think after I had to meet our original angel investor, it was a guy named John Phillips, who’s still on our board now. And I had to meet John in Toronto for coffee and I had to convince John that I was the right person for this.
And I think after trying to convince everyone over a matter of months, coupled with the fact that Tobi had already known me well, both as a friend but also as a merchant on Shopify, as a customer of Shopify’s, in early 2010 I joined the company. And I think my original title was VP Bus. Dev. and legal counsel or general counsel or something like that. And that was about 11 years ago.
Tim Ferriss: Wow. 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. And we spoke in brief about one before we began recording. That is, how certain investors were able to get on your cap table as they call it, becoming part of the equity structure of the company. But do you have any memories from the early fundraising days, whether it’s from the Shopify side of things, from the investor side of things, any particular items or memories stick out to you?
Harley Finkelstein: Yeah. Around the summer of 2010, we decided that it was time for us to raise our Series A. And that interest or that appetite to raise some money, it was based on the fact that we’d began to understand our business, not completely, but at a deeper level than I think we previously did. We understood what were some of the puts and takes of the company, how to spend a dollar here to make a $1.80 on the other side. And therefore, the more dollars we had on the left side, the more $1.80s we get on the right side. We also realized that we were 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 are we already working with indirectly? Whose counsel are we already taking without even realizing it? And I think around the time, maybe a year earlier, Bessemer Venture Partners had written this white paper, which I think is still available online. It’s called The 10 Laws of SaaS Businesses and the white paper, it was great. It was important for a couple reasons. One, it gave us the nomenclature that even today we still run the business with, things like monthly recurring revenue and ARPU and customer lifetime value. And it provided us with a set of calculations and formulas that allowed us to know whether or not our business was healthy or not.
Tim Ferriss: Just a quick pause just for acronyms, for those who might not know, SaaS is —
Harley Finkelstein: Software as a Service.
Tim Ferriss: Software as a service. ARPU, average revenue per user, is that right? Am I getting that right?
Harley Finkelstein: Yeah. And then customer lifetime value is CLTV. It was instructive, it was valuable. So funny enough, we were already working with Bessemer, even though Bessemer had no idea that we were doing this. Now, maybe this is an entire pitch, 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 we knew we wanted Bessemer around and they ended up leading the series A. A bunch of other people had heard we were raising and we got some inbound interest, which was really great. But there were two others in particular that really set themselves apart.
And one, I found out earlier today from you, actually, you have a connection to, I didn’t actually know this story until this morning. But at one point in the middle of the fundraise, in the middle of deciding what the round was going to look like, and who are 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 ByWard Market in Ottawa, right above a restaurant. Wasn’t a necessarily fancy office, but someone showed up and his name was Aydin Senkut from Felicis. And he showed up. And I know now, if you want to do a deal, you show up.
But at the time, no one had really ever shown up at our door. Certainly not some well-known, highly respected investor from Silicon Valley who cut his teeth as an early employee at Google and had this great reputation, but Aydin showed up. 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 was such a wonderful, him and I talk about the story all the time now, because it’s just a great story, but that’s Aydin in a nutshell. Where others would write an email or phone you or want to do a video conference, his style is, you just show up. And he ended up coming to the series A, which I think and hope that was a really good investment for him. And FirstMark also, FirstMark Capital from New York also joined, same type of dynamic. They simply — Amish at FirstMark really just showed up and helped us the second we encountered them and that was our series A, it was a $7 million round. I think it was a $25 million evaluation, maybe 25 post. And that was our series A in 2010.
Tim Ferriss: Aydin, for people wondering is, A-Y-D-I-N last name Senkut, S-E-N-K-U-T. On Twitter is ASenkut and he’s an investor in lots of stuff. You’ve got Shopify, Fitbit, Pluralsight, Rovio, Notion, and many others, very successful, very nice guy also.
Harley Finkelstein: Here’s an interesting story about him. In the early days after he invested, one of the things we needed was, we needed a merchant that was going to sell it to scale because we needed to test the resiliency, but also the scalability of Shopify. And Aydin heard this and immediately connected us with Rovio. I don’t know if you remember this, but Rovio’s major hit is Angry Birds. Angry Birds was flying in, I think it was 2011 or something like that. And the brand, I think they were from Finland, if I’m not mistaken. The brand just blew up. They had Angry Birds Cola and they had Angry Birds clothing, but their plush toys was one of the most hottest selling items of the season. And hearing that we needed to test the scalability, but also to show that you can sell at scale on Shopify, Aydin connected us directly with the Rovio people and within a matter of a week or so, they had launched the Angry Birds store on Shopify. And that really was one of our first major blowouts in terms of demonstrating the scalability of Shopify and that’s the investor he is.
Tim Ferriss: I have to wonder what his pitch was to them. I’m pretty sure it wasn’t, “They want to see if their software will break.”
Harley Finkelstein: I can’t imagine it was. I assume it was a lot more of, “Hey, these guys are amazing, the best platform, ever. Of course, they have lots of at-scale stores and you don’t have to worry about them.” But what’s interesting was, Aydin had come to you because of our existing relationship. And you had made the intro to us from Aydin and I actually didn’t know that until this morning.
Tim Ferriss: Yeah. It’s pretty wild. And just as background context for people who don’t know, Tobi and I had met in 2009 at something called a RailsConf, you mentioned Ruby on Rails. And for simplicity, let’s just call it RailsConf or developers conference. Why I was there was, I think I was largely there just a sideshow curiosity, but that was two years after The 4-Hour Workweek. And it had struck a chord in Silicon Valley and rightly or wrongly, there I was in the green room, meaning the backstage room or a location where speakers hang out before they go on stage. And that is where Tobi and I had our first meaningful conversation. Then later, was lucky enough to become an advisor to Shopify. And from that point forward, was along for the ride.
Harley Finkelstein: You actually gave us one of the best pieces of advice as an advisor. I don’t know if you remember this and I’m going to butcher the exact quote you gave us, because I’m sure it was far more eloquent than what I’m about to say or articulate. But you said, “What you guys are building is great. The problem is that most people that think about entrepreneurship, immediately think it’s either too complicated or too expensive or too difficult. And that if Shopify was going to be something important in the world, we not only had to build great software. We also have to convince the world to try their hand at entrepreneurship.” And that was one of the biggest pieces of insight, certainly in the early days, we ever had received. And that was from you. And we’re eternally grateful for that.
Tim Ferriss: I appreciate you saying that. The Build a Business competition, I would love to know how you think about it when you’re remembering it, because I remember the conversations very early on with you, with Tobi. I remember walking past, up and down the sidewalk next to this Thai restaurant in San Francisco. I remember exactly where it was. 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 Build a Business competition. But how would you like to contextualize this for people, because it is a good example of a way to differentiate yourself and generate both attention for brand purposes and user signups that might be instructive for folks who are trying to find a way to stand out from the noise?
Harley Finkelstein: Yeah. Are you familiar with the Geoffrey Moore book Crossing the Chasm?
Tim Ferriss: Yes.
Harley Finkelstein: Okay. So fundamentally, if you were asking me what Build a Business did for Shopify, it allowed us to cross the chasm from early adopters that were using it. I mean, the neat part about Tobi writing the software in Ruby on Rails is we got some early traction from that Ruby on Rails crowd. That was great, but the mainstream had never heard of Shopify, had never heard of any of us. It 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 is a great idea. But what about people that have not yet made the decision? Because for 99.99 percent of the world, entrepreneurship is out of reach.” If you don’t know an entrepreneur, if you have never started a business yourself, it does feel intimidating. It does feel out of reach.
Through this conversation somehow we landed on this idea that what if we created a competition as a proverbial kick in the butt to convince folks to try entrepreneurship and use Shopify and the store with the highest sales would win $10,000. I distinctly remember you saying, “Yeah, that’s bullshit. $10,000 is nothing. You’ve got to give out $100,000,” which was most certainly more money than we had in our accounts. Certainly more money than any of us had combined. You could have said a billion dollars and it would’ve been the same thing to us. That’s how much $100,000 was, and frankly it —
I now realize how much foreshadowing that was in terms of the company that we are trying to become, which is the world’s entrepreneurship company. We wanted Shopify to be more than a software company. We wanted to create a movement. We feel that the world is better with more entrepreneurs. How do we get more people to try their hand at entrepreneurship?
In the same way, one of the amazing marketing hacks that Nike did, and they deserve all the credit in the world for this. They convinced the world that anyone that has a body is an athlete, or can be an athlete. That was completely different than the previous iteration of who wore those early iterations of Nike shoes, of running shoes. It was for people that lived in Oregon and went to Oregon State and ran track and field. But they convinced the whole world that if you have a body, you were absolutely an athlete.
I think what we began to do through this Build a Business competition was try to convince people that if you have ambition, you can be an entrepreneur. We did that by virtue of frankly, bribing them to start a business by offering a $100,000 prize to the store that sold the most.
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 a $100,000 check. 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. But I think it was, I don’t know, the headline’s off-hand, but it was something like, “A startup creates their own startup competition,” and it was a really meaningful thing for us and the Build a Business competition ran for five years after that.
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. So it’s a part of our story. It seems like it was just a campaign, but it was so much more than that. It defined us both internally and externally as a company that thinks differently about entrepreneurship.
Tim Ferriss: Yeah. In retrospect, and also at the time, the sort of the logic behind pushing for the 100k, there’s psychologically a very big difference between five-figure, six-figure, and seven-figure. 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 $50,000 puts you in the category of — I’m using that arbitrarily, but like 10,000 or $50,000 puts you in the category of business competition and there are other business competitions that have done 60,000, 70,000, there is a day and night binary difference between that and being in the category of one, which is the largest X ever, or the first Y ever.
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 No. 4, until you have a first draft, the whole thing seems overwhelming and unwieldy because there’s nothing to refine. But as soon as — and I remember this, as soon as the sort of parameter as a draft became not could we, but what would it look like to have a $100,000 prize and this competition, then you start to find ways to mitigate risk.
You start to find ways to look at it as an expenditure over time, and you realize that it’s certainly not going to be a $100,000 loss if it’s a failure. If you shoot high, I think it’s Larry Page who is fond of saying this, something like this, but you know, “What a lot of people miss is that if you aim really high, it’s very hard to fail completely.” Right?
Harley Finkelstein: Yeah.
Tim Ferriss: Then you guys did it. You had The New York Times coverage and you were extremely newsworthy because you had the biggest ambition and you were also breaking ground as a first.
Harley Finkelstein: Yeah, it was ballsy, but the thing that actually is super interesting is what we didn’t necessarily realize at the time you only have to pay it out at the end of the competition. So you don’t actually need $100,000 when you get started, you just have to be able to acquire enough revenue over the period of six months to actually pay that out eventually. That was sort of an interesting, “Oh, right.” 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. I think you and I talked about competition law before, in advance of it. So like, we actually couldn’t necessarily offer it everywhere because of some — like with what they call sort of gaming law.
But absolutely it was bold. It was ballsy. It was an interesting thing that a small company was doing and we had 1,300 contestants sign up for Build a Business in 2010. The winner was a company called DODOcase which made the most beautiful iPad cases and ended up Obama was using one at the time and he was photographed using his DODOcase.
They also did some really cool stuff like they completely rejuvenated the bookbinding industry, which had been effectively shut down in San Francisco. They brought these bookbinders together and started making iPad cases. But the neat part was the big takeaway from year one was some of these businesses were growing so big at the $100,000 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 prizing to be once-in-a-lifetime opportunities, to be things that basically money can’t buy. A lot of that was connecting the winners with some of the most interesting people in the world who were incredibly generous with their time and wanted to kind of help out. We brought on people like Seth Godin, and we brought on people like Gary V, and we brought on people like Richard Branson and Tony Robbins and Marie Forleo and Debbie Sterling and Tina Eisenberg. We brought these incredible mentors aboard and instead of giving them $100,000, we said, “Hey, the winners get to spend a week with us and a bunch of really interesting people on Richard Branson’s private island in Necker, in the BVIs.
I think the last year we did it, we had over 10,000 contestants. We’ve actually since then have done a Build a Bigger Business competition, which is million-dollar businesses who can actually grow the fastest, 10X, 20X. One of the winners of the last one was Gymshark, who as of last week is now a billion-dollar brand.
Now, these businesses may have started regardless and despite Build a Business competition. I mean, Ben from Gymshark probably would have started no matter what, but what the competition fundamentally did was it provided this catalyst to get started right now and that is why I think it was such a powerful initiative and movement for Shopify. We are forever grateful to you, Tim, for really bringing us that because our trajectory has been forever changed because of Build a Business.
Tim Ferriss: It’s been so much fun and such a pleasure. I’m just taking a note for myself here. I’d love to talk about the future of retail. I’ll tell you something, I don’t think you know, which maybe you do, I don’t think so though because we haven’t talked about it, is that I remember when Shopify went public and spending time there in New York at 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 stake off the table and it’s always been this huge source of guilt and shame for me.
And so I was eyes wide open when in, let’s say late March, early August, I decided to come back in and put the Shopify jersey back on and to buy back into the company. So I am as bullish as I’ve ever been. Obviously, I’m not a registered investment advisor, blah, blah, blah. I’m not giving investment advice, but I feel like that sort of a psychic load of guilt and shame has been lifted, which I’m thrilled about. I wonder if you could talk to the extent that you can, what has happened in the last few months and the future of retail?
What are the things that people are missing? What are some of the sort of maybe assumptions that you have or things that you think are coming down the pike? You have such a unique vantage point because you not only seeing Shopify, much like a Stripe is not just seeing Stripe internal finance. It’s like they get to see who is growing fastest or any payment processor for that matter who is handling this type of stuff. So you get this incredible perspective on the ecosystem of a million or a million plus companies, not just Shopify itself if I’m phrasing that in an intelligible way. So how would you talk to what has happened in the last few months and the future of retail?
Harley Finkelstein: Yeah. So first of all, you said this earlier, but this idea that the year 2030 has been pulled into 2020, that’s a real thing. What I mean by that, what I say is that the retail dynamic that would have existed, meaning percentage of total retail that is done online, laggers that have begun to digitalize their business from a commerce perspective, that has all happened rapidly in three months.
And so if you look at retailers, excuse me, ecommerce as a percentage of total retail, when I joined Shopify, it was approximately five percent, something like that. These are US numbers, last year ecommerce was about 15 percent of total retail. So we’ve grown about 10 percent in like, I don’t know, 10 years. We’re now at close to 25 percent. So since March, the amount of acceleration in shifting total retail to online retail has been dramatic.
One is, I’m surprised by how quickly that happened. I’m not surprised where we ended up, because I think we would have ended up here anyway. Two things have happened. The first thing that has happened is you see two types of entrepreneurs existing right now. I mentioned these terms earlier, but it’s worth repeating.
You have these resistant retailers and entrepreneurs and brands who simply did not adapt and pivot fast enough and they are suffering. You’re seeing iconic brands, whether it’s Barneys or it’s J.Crew, name your pick, that have gone out of business, because frankly they simply didn’t see the future retail coming in the way that it has materialized.
So for example, a lot of these brands that went out of business, they lamented the fact that ecommerce was hurting, like their ecommerce efforts were hurting their offline commerce efforts, which is ridiculous. If you talk to any of the guys at Allbirds, for example, they couldn’t care less if you buy it in-store, online, or on social media, they just want you to buy their shoes.
Their online store maybe a catalog for their offline store, or their offline store may be a showroom for their online store. They are completely channel-agnostic. They just want you to have a great experience and buy a great pair of shoes from them. But a lot of the big brands didn’t and they resisted this change; they fought it.
Then you have this other category, these resilient retailers. We talked about Gymshark earlier in the context of Build a Business, the day that COVID hit, they’re based in the UK, and they were told that gyms where people work out, were going to be closed. They rebranded their homepage as Homeshark to the Gymshark.
They immediately changed their content and their distribution and their influencers, and everything about that company changed within 24 hours because the world changed. Immediately people were not doing the same thing as they once were. You see that across a whole bunch of different categories across Shopify, these great brands that have just completely pivoted.
You see restaurateurs that are doing meal kits, and they’re turning their restaurants into wine shops if you can’t go in there. You’re seeing grocery stores that historically never even came close to Shopify — it wasn’t a vertical of ours — are now signing up for Shopify and doing their top 12 most popular items and have a beautiful store.
Chipotle has a store on Shopify right now where they’re connecting Chipotle consumers with the farmers who are there are their suppliers. They’re basically creating a Chipotle farmer’s market for consumers on Shopify.
So on both sides of the coin, you see totally different stories. I want to focus on the resilience side because frankly, that’s the real story here. The real story is that the consumers generally have now decided, 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 brands selling direct to the consumer. And so you have this new retail model and it’s not necessarily just going to be online or it’s going to be offline. The future of retail will likely be retail everywhere.
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 video game, 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 opened, you ran in to grab a video game, and then you left. That’s how it worked. The retailers have historically always dictated to the consumer how, when to purchase.
What’s happened now is consumers are saying, “No, no, no. I want to purchase in the way that it’s most convenient for me.” A lot of that is online, but it’s also offline, and it’s also across marketplaces and social media, but fundamentally, commerce has been changed forever.
Now, will the growth rate of ecommerce continue to grow at this pace? Probably not. I mean, 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, four months, there’s no going back to the way it was.
There is 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 store’s online stores. I actually think this is one of the most exciting times for retail of the last, I don’t know, call it 150 years, but it is a tale of two worlds and I hope some of these resistant retailers begin to simply wake up and realize that everything has changed and they don’t have to be left behind.
Here’s a cool example. When you think about these resilient retailers, you often think of the Gymsharks, the Fashion Novas, the Bombases, the Tommy John underwears, like these amazing, incredible, iconic DTC brands, but we’ve seen Heinz Ketchup go direct to consumer during the pandemic. We’ve seen Lindt chocolate, Snickers, Schwinn bicycles.
Some of these brands are brands that I have personally been calling for five or 10 years to try to convince them to come on to Shopify to sell direct to consumer and they just never did it. 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. 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 don’t think it’s going to happen.
Tim Ferriss: Yeah, I don’t think it’s going to revert to at least what the previous normal would be anytime soon. I remember the night that I decided to jump back into bed with you guys. It was very specific. I had a couple of things that happened. A, you guys had been unfairly — well, as far as I’m concerned, unfairly punished in when you suspended guidance.
Then the second thing that happened is I tried to order coffee filters on Amazon. 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?
Harley Finkelstein: Yes, totally.
Tim Ferriss: You had mentioned renting customers. I have friends who run very large ecommerce brands and small, medium, and large brands everyone would recognize, and a lot of them have bought Amazon stock once they saw a double-digit percentage of their sales move to Amazon, whether they liked it or not. To me, what that says is a lot of people, having that experience with the coffee filters, a lot of companies were going to get caught between a rock and a hard place where they couldn’t email their customers and say, “Hey, come over to this other store,” if they had one, because “You’ll have to wait a month on Amazon otherwise.”
They were dependent on that rented customer base they couldn’t contact directly. I thought, “Okay, at the very least, this could be a fatal shot, like a headshot for a lot of companies, but for a lot of them, it’s going to be a flesh wound. It’ll be like a shot in the leg and they’re going to say, ‘Holy shit, we at least need, at least need a plan B so that there is a Google discoverable storefront for our products if this ever happens again.'”
That was sort of the assumption, not to mention the fact that if anybody — again, this is just sort of me reading stuff on the internet, if anyone from a large tech perspective wants to integrate some type of ecommerce 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, Facebook or whoever, it might be, their options are pretty limited. I mean, they can build in-house or they can partner with someone who’s already built out the infrastructure.
Harley Finkelstein: The neat part about that is we don’t want to sell ads. 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 Howies, or to do any of these things. The neat part about our positioning is that we simply want to encourage more people to try their hand at entrepreneurship and to become retailers.
The idea that, to your point earlier on the pandemic, I think a lot of consumers are thinking about their local small businesses, well, we all are. I mean, our communities are now becoming far more important because frankly, like I spent a hundred nights on the road in 2019; I’m going to spend five nights on the road in 2020.
My community here in Ottawa is becoming incredibly important. So whenever possible, I want to support my local stores, my local restaurants, my local cafes, as much as I possibly can. 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 businesses 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, the money that we’re using to buy stuff with is going to the people that actually are behind those companies. That in order for retail and commerce to thrive long-term, it needs to be in the hands of the 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. Actually, I think one of the great things that will come out of this is this consumer trend to support independent businesses as much as possible. I don’t think that’s going away after this.
Tim Ferriss: Yeah. If it’s easy. If it’s easy and that’s a super key component of all this. Let me ask you about mentors and actually mentors in a different capacity than we’ve been referring to them and that is coaches. So it seems like, and this is something I wasn’t aware of, but that you have coaches internal at Shopify available to folks. The story I read talks about Cody Fauser I guess it is.
Harley Finkelstein: Mm-hmm (affirmative).
Tim Ferriss: Is that correct? His experience with coaching, but how do you use coaches and how are coaches used at Shopify?
Harley Finkelstein: Yeah, so Cody was the original CTO, and one of the first guys of the company, and certainly someone who’s been a big part of the Shopify origin story. At a particular point, he was running engineering and he realized that his team was getting bigger and bigger, and he didn’t necessarily have all the tools he needed to be the right leader. But in this sort of theme, in this sort of lens of we always requalify for our jobs every year, if we want to keep our jobs, he decided —
Tim Ferriss: Before we go back to Cody, I apologize to interrupt. But since this has come up a couple of times, what does it mean to requalify for your job, you’re getting effectively hired each year anew? I mean, is that metaphorical, it’s more of a loose philosophical guidance, or is there actually a process for evaluating whether you qualify or don’t qualify? What does that mean?
Harley Finkelstein: It’s a very valuable, personal growth sort of philosophy that this idea and I can’t speak for everyone, but I certainly speak for myself, and I know Tobi feels the same way in his role. I need to be on every single year. I still have to be the best possible Chief Operating Officer for Shopify. If I am not, that means that someone else should take my role.
The reason that’s important is because the pace that Shopify is growing at, it has been growing every single year since I joined, certainly, I have to keep up with it, but I also have to keep outpacing it. And so there’s a lot in that. I mean, Shopify again, went from being an ecommerce provider for small businesses to being a retail operating system. We have a billion-dollar capital business.
We have a fulfillment business now. We’re cross-platform. We’re publicly traded. And so it’s a really, really wonderful model of which to gauge whether or not you are growing at the pace, because if you say, “Well, are you growing every year?” Most people say, “Yes, I’m growing. I’m learning new skills every single year.”
But if I use the lens that if the greatest chief operating officer in the world walked in to see the board of Shopify and said, “Hey, I want to be your COO,” I need to know that I am still the right choice. This idea of requalifying for your job from like a philosophical perspective has just been incredibly valuable because it means that if I grow at the same pace of Shopify, I still may not necessarily be the right person for next year.
So I have to almost outpace Shopify’s growth, which puts the onus on me and all of our leaders to grow at this incredible rate. And whether you call it requalification or you call it disproportionate personal growth, that is something that is baked into the culture of Shopify, unequivocally. 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.
Tim Ferriss: I interrupted you. You were talking about Cody, so I want to take us back to Cody. It seems like coaches are one of the tools in the toolkit for staying ahead or front running.
Harley Finkelstein: Yeah, right.
Tim Ferriss: That’s right.
Harley Finkelstein: 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. Then he introduced Tobi and I to it and we really started getting a lot of value from it. 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 was Cam, and bringing him on full-time and he really helped coach the exec team at Shopify.
Tim Ferriss: Very quickly, explain, sorry, I’m going to keep interrupting you —
Harley Finkelstein: Yeah, please go ahead.
Tim Ferriss: — but it’s my job. What is this coach doing? Because there are, coach is 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, or a great teacher, and then there are different subjects. What did this coach do with you guys?
Harley Finkelstein: So what you’re saying is correct, which is that not every coach is the same. And frankly, one of the problems with coaches, in general, is that nomenclature, that it doesn’t take very much to call yourself a coach. There is no medical school for coaching. I mean, you can take a program or get a certificate, but generally, not all coaches are going to be the right fit, the right match. They aren’t 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 a 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, the Shopify company, the people involved, it would put them at a disadvantage for actually helping us achieve this development that we were looking for.
And so we ended up just hiring this one particular coach, Cam, full-time, and he was coaching a few of us. 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. That eventually led to us saying, “Hey, what if we actually created a team of coaches at Shopify so that anyone who wants to, or frankly, needs to have a coach can do so. The onus isn’t necessarily on them to find a coach, we’ll have a group of coach. They can sort of interview a few these coaches that we have on staff, but that they work full-time at Shopify.”
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 see, I have a new coach now, her name is Deb and it’s been an amazing journey for me. And in fact, I kind of can’t understand — I mean, I talk 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.
Tim Ferriss: Well, I think it hearkens back to the quality assurance and the difficulty of vetting in part. So, let’s talk about, just to give people who aren’t going to be able to hire full time because there are a lot of companies or people who won’t be able to do that, but 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. What actually happens? Is there a scorecard? Is there communication in between? What does it look like? And I’m most interested in what it looked like before you hired them. I understand the reasons for hiring them, but at some point, you guys thought to yourselves, “This is so valuable. It could be even better. Let’s hire them.” So they were already demonstrating value. What did the format, or what might the format look like?
Harley Finkelstein: One thing that the coaches that I have seen have — one of the things that they have done, which I have found very valuable is, they use a metaphor. So for me, I’ll just tell you what the metaphor is because I think it’s valuable for listeners. My metaphor was, I wanted to develop from a Mossad commander who’s always doing everything all the time and a jack of all trades, into more of a sensei whereby I can play the role of — I can work with really, really talented people, I can explain to them what destination they need to get to, but in terms of the journey to get there, I can rely on them, I can trust, but verify. I can provide them with some breadcrumbs to make sure they’re going in the right direction, but that inevitably they will get there on their own.
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 have to work on some of that, some 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 Tobi about the trust battery metaphor at Shopify, where everyone starts at 50 percent trust battery, and through their actions, 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 coaching style that our coaches use is called the integral method, which is a bit of a hybrid of a bunch of different coaching styles, but that metaphor, to know where I am right now, to know where I want to get to. And then every two weeks, an hourly basis walking through, “Okay, give me some examples of how you’ve demonstrated more of that sensei type thinking and less of the Mossad commander thinking.” Holding me accountable to that, when I provide them with something that is challenging to me, having them workshop with me the right way to do it as a sensei, as opposed to a Mossad commander, man, that has been so, so helpful.
It also feels like when you do bring them in, and I’m not suggesting everyone needs to hire a coach full time, because actually, I have a lot of friends who have third party coaches who just, 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? Do you want to get better in terms of your craft? I find the ambiguity that most people bring into coaching is not helpful at all. And if you were clear about, “Here’s what I want to work on, here’s what I suck at. And please call me out on my bullshit with this stuff, or hold me accountable to these things.” That I think is where you get the most successful dynamic with coaches.
And frankly, you may outgrow your coach. Every couple of years it may be time to get a new coach who has a different skill set, but I have to say, if I had to distill down one of the things that has allowed me to get to where I am at this point with my career and certainly helped me lead Shopify, coaching is up there in the top three or four things that I’ve done.
Tim Ferriss: What else would be up there? Any others come to mind that are in the 80/20 distillation of things that have really moved the needle? Any other items come to mind?
Harley Finkelstein: Yeah. This is maybe a personal thing, but even as a kid, I always had anxiety. I never had a term for it. I never understood exactly what it was. I just knew that I had this thing and I knew it was anxiety because I was always thinking about, what’s next, the future, as opposed to, what people often talk about a depressive state, which is looking backwards. I was always looking forward and I had experimented with some mindfulness practices and some meditation in the past. But because I was anxious in general, I was anxious about meditating, meaning I was always looking for some sort of quick fix that if after 10 minutes of meditating, I didn’t find enlightenment, I thought it was broken. I thought it wasn’t working for me.
Which sounds absolutely ridiculous, right? Of course. But meditation has also been something that I have committed to over the last, probably since 2014. So going on six years now, every single morning, it’s either 10 or 15 minutes, depending on how much time I have, and it has made me — I’m by no means, as you can hear from the tone of my voice, I’m by no means laid back or a “chill” kind of person, but it has made me more thoughtful about how I want to expend my energy. And it has allowed me to focus on the things that are most important, both on my personal life, but also with our business. And man, I know you talk a lot about mindfulness practices and meditation on the podcast, but I am someone who for years just did not subscribe to it. And it was because I was looking for some sort of quick fix and it 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.
Tim Ferriss: Meditation is a lot like sports in the sense that there are many different flavors, right? There’s badminton, there’s curling, of course, not to be forgotten.
Harley Finkelstein: Thank you. There’s hockey, too.
Tim Ferriss: You’ve got MMA, you’ve got hockey, you’ve got all sorts of different sports, darts. And meditation, similarly has many, many, many different approaches. What do your sessions look like? Do you use an app? Do you use transcendental meditation? Do you use open awareness? What flavor of meditation do you use most consistently?
Harley Finkelstein: So, it’s funny, I had been historically using just Insight Timer and just doing a 15-minute counter with a little bit of white noise to block out whatever’s happening around me. But going back to my power extrovertedness, I have found that this pandemic has been kind of lonely for me and I don’t mean that in a severe way. I’m home now with my amazing wife and my two amazing kids and I have my family around me, but there’s a certain lack of social interaction that is missing for me. And so, early in March for the first time ever, I ended up just going to the guided meditation tab in Insight Timer, just because I 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’ve talked with Jack Kornfield, Sharon Salzberg, David Gandelman. There’s just some amazing — I’m just trying to look at who else. Sarah Blondin. There’s just some amazing guided meditation coaches on Insight, or frankly, I mean you can probably do it on YouTube as well. And I actually have found that guided has been, it’s like a warm hug for me in the morning where I hear this really wonderful, calm voice taking me through a 10- or 15-minute sit. And I always end up on the other side so much better.
And so I started with counting breaths. So now trying to do a little more mantra-based TM style stuff. But the truth is, it really depends on the day and I’m trying not to be too hard on myself about that experience. That if on a Monday, I had this great sit and I come out completely mindful and relaxed and focused. On Tuesday, if I don’t have that same experience, I don’t want to forego Wednesday. And the way that I’m able to have consistency is just take it easier on myself around my own version of what a successful sit looks like. And I think today a successful sit for me is really just the ability to sit for 15 minutes consistently every single day, no matter what I feel afterwards.
Tim Ferriss: That’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 out that time, especially if you’ve operated in sixth gear for a very long time, which you and I both have, it’s very easy to try to cram as much as possible into your waking hours. It’s easy to do and it’s a compulsion as much as it is anything else. And by blocking out 10, 15, 20 minutes to do nothing, you build in, I think a sense of luxury in so much as you are not rushing yourself. And that has many downstream effects, even if you’re just like thinking about your to-do list and staring at the ceiling for 20 minutes.
Harley Finkelstein: Yeah, totally. I actually do that.
Tim Ferriss: Sitting there and you’re not on a keyboard, you’re not staring at a screen, you’re not checking your phone.
Harley Finkelstein: Yeah, I totally agree with you, which is actually one other thing that has been very valuable to me is the value of scheduling and being fairly meticulous about my calendar. And this is going to sound totally lame, but I have family time blocked out on my calendar, I have walks with my wife blocked out on my calendar, which again sounds completely lame and unnecessary, but what it does do is that pop up comes up on the top right side of my screen and suggests, “Hey, it’s family time.” Or, “Hey, it’s a walk.” My wife Lindsay, who you know, is also an entrepreneur. We’re very busy; we have two little kids.
And 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 that we skipped this walk to do something else. So the question is, was the thing we skipped that walk for as valuable as the walk would have been? And the answer is most times, no, they’re not. So actually being meticulous with our calendars and our schedules, especially with two entrepreneurs in the house and two younger kids, that has been amazingly valuable to us.
Tim Ferriss: Yeah. I could not agree more. And only in the last six to nine months have I been using, with my girlfriend, a shared calendar just for the two of us.
Harley Finkelstein: Totally. Yeah.
Tim Ferriss: And it has been such a stress reliever because she is also an entrepreneur. And if you somehow, at least in my case, delude yourself into thinking that you’re going to figure it out when you get there, it’s probably going to slip through your fingers. And having it in the calendar just prevents forgetting and then overbooking or fill in the blank with half a dozen things or a dozen or a thousand things that could crowd out that recovery time and that family time and these various self-care practices that are so important for everything else to work smoothly.
Just a couple more questions for you, and then we can bring this round one to a close. I’m curious, what contemporary CEOs or COOs, 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 could emulate a little bit? That’s someone I could learn from? Or that’s a good person to watch?” Et cetera.
Harley Finkelstein: Yeah. I mean, there’s some obvious ones. I think one of the cool parts of being in my position, this is a new thing for me, but one of the cool parts is using my email address. If there’s someone interesting, I can actually get in touch with them. That’s brand new to me. That’s not a flex or some sort of humblebrag. 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 admire from afar, like Bob Iger. I mean, I’ve never met Bob Iger. I think he’s just incredible. Or Phil Knight. I think these are incredible humans, but there are some companies that I think are just run by people that I really like, I really think are doing it for all the right reasons. A lot of them are people that are in the Shopify ecosystem, people we work with. Obviously, we’re quite close to the folks at Stripe. You mentioned them earlier, Patrick and John. I mean, they’re absolutely driven to do incredible things, but also build an incredible company. I think Ben at Pinterest is doing an amazing job as well in that way.
A lot of the people that I really look up to though are not necessarily in tech, per se, it’s people that I just think — one of the people that I really like, it’s a mutual friend, I love talking to Chase Jarvis. I know Chase is a good friend of yours as well. Every time I talk to Chase, I learn something completely new. Or Daymond John, who I know is also a mutual friend. I mean, Daymond built FUBU, he didn’t build a tech company, but every time I talk to him about something unique and different, he tells me a story, an anecdote about how he got a shirt on LL Cool J for a music video. And from these what seems like random stories and anecdotes, I’m able to find such great value and such great motivation to think about things in a completely different way.
But, is there someone in particular that I’m trying to emulate entirely? Not really. In the same way that before I had Bailey, our four-year-old daughter, I wanted to talk to people that I really felt were great, great dads and great parents or someone who was a great spouse before I got married. I’m trying as much as possible to take a bit of an approach that I can have as many mentors as I can handle and I can pick one thing from each of them. The interesting part is when you find people that are really, really good at one particular thing, they tend to be fairly spiky, meaning they may have an incredible strength, but also have a whole bunch of weaknesses. And so the model that I’m trying to create now with mentors and advisors and people in my life are to take something special from each particular person and use that in my own day-to-day.
I try to be a bit of a generalist as much as possible, as opposed to specialize in one thing. I think that there’s a little bit of an anti-generalist theme right now, certainly in Silicon Valley. But I don’t purport to be well-rounded, but I am trying to be well-rounded about the stuff that really matters to me, whether it’s leading, whether it’s the business, whether it’s inspiring the future entrepreneurs of the world, or it’s about — I’ll give you a quick story. We have this new show that we just launched on Discovery called I Quit! And it’s Shopify’s — we have a studio called Shopify Studios with the single mandate to create the most inspiring and authentic content about entrepreneurship in the world. And you’ll never hear us mention Shopify on the show because that’s not what it’s about. It’s about entrepreneurship.
And before I got on the show, I sat down with Daymond 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 do you give, which is digestible, but also doesn’t come off as overly obvious?” That’s the way that I tend to do things when there’s something that I want to get really, really good at, I’ll find the three or four people who may not be the obvious experts in it, but I understand there’s an angle to them that I really want to emulate, and then I’ll just ask them. And it’s pretty cool that I can do that now.
That was something that, for those of you listening that do email 100 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 “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 was before anyone even heard of Shopify. It’s been a really important part of my life. Yeah.
Tim Ferriss: Yeah. Seth is amazing. Seth Godin, for people who are curious, I 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 probably low.
Harley Finkelstein: Pretty low. I would say pretty low, yeah.
Tim Ferriss: There is a, what you might consider doing is a bunch of free work for somebody and just sending it to them. And that’s actually how I’ve ended up hiring a bunch of people. I’m not saying do that to me by the way, because I’m not planning on hiring more folks, but if people look up the name Charlie Hoehn, H-O-E-H-N, and my name, he’s written about the experience that we had. He also wrote about The 4-Hour Body launch, if you people are interested in that.
Harley Finkelstein: That’s cool. Yeah. One thing that I’ve always found valuable, especially in the early days of Shopify was, if I want to connect with someone who I knew was incredibly busy and the likelihood of them responding was very, very low, I would figure out what is the thing that is most important to them right then? And in the case of, let’s say it’s an author, obviously they have a book release coming up. I would figure out how I can be valuable to them. So asking someone, “I live in, name some random city, I want to host a book reading or a chapter reading in my community and I’ll buy 30 books or 50 books.” Even if it’s not 3,000 books, I find that if you can add some value to something that is so damn important to them right then and there, and with social media, it’s easy to figure out who cares about what at what time, man, is that an effective way to spend some time.
Tim Ferriss: Yeah, totally. And there’s a book called The Third Door, I would recommend people check out as well, which has some very funny stories and very effective advice in it, which is about taking the path less traveled when it comes to contacts of that type. Harley, let me ask you, because we’re talking about these various leaders, are there any biographies that you, I don’t know if you read biographies, but are there any biographies that you’ve read and found particularly impactful or influential?
Harley Finkelstein: Yeah. I’m not sure it’s a biography, but one of the best books I’ve read, I read it a couple of years ago is Shoe Dog. And I’m not sure, have you read Shoe Dog?
Tim Ferriss: I have it 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.
Harley Finkelstein: It is awesome. It’s awesome for anyone who’s building a company, anyone who’s an entrepreneur. Or frankly, anyone who’s just interested in the idea of ambition. One of the reasons that I have fallen in love with entrepreneurship and one of the reasons that I’ve dedicated my life to creating more entrepreneurs with Shopify as the vehicle to do so is because I’m fascinated with ambition. I’m fascinated with how people find ambition, keep ambition, increase ambition, and unfortunately, as well, lose ambition. And the story of Shoe Dog and how Phil Knight was so determined, I think it’s such an amazing story.
And the cool part about it is I think because Phil is where he is right now and has really not proved to anyone anymore, he was able to be incredibly candid. One of the problems I find particularly about autobiographies is that often you end up seeing the highlight reel of people’s lives, especially people that are not at the end of their life or close to the end of their life, where they feel like they still have to flex a little bit. They still have to show off about how great they are. What I love about Shoe Dog is there’s this incredible modesty and humbleness about the story, which is like, this was not pretty and there were 12 different opportunities for this whole Nike thing to fall apart and he goes into the details and tells the stories that I just found it to be so fascinating. It’s a great book. And you can get through it in like five days if you’re interested in it, because it’s just, you can’t put it down, but that’s probably the best one that I’ve read recently on that topic.
Tim Ferriss: I have to read it and I’ll tell you why, which is not a reason that most people would probably cite. And that is that it was written, we could say co-written, but in reality written by one of my favorite authors whose name people will not recognize. And that is J.R. Moehringer. So he is the collaborator, so to speak, who wrote Phil Knight’s memoir, Shoe Dog. And for people who want to look him up, you can find him on Wikipedia, J.R. Moehringer. M-O-E-H-R-I-N-G-E-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 —
Harley Finkelstein: Andre Agassi, yeah.
Tim Ferriss: Andre Agassi and it blew my mind. It was so good. So engrossing,
Harley Finkelstein: You’re the third person to recommend that to me. I love tennis, I play tennis, but I actually have not read that. I’m actually going to write that down too.
Tim Ferriss: So now you know, it was in effect written by the same person. And for that reason alone —
Harley Finkelstein: You’ve got to read it.
Tim Ferriss: I will read it.
Harley Finkelstein: That’s cool.
Tim Ferriss: Because I believe 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. Yeah. If I could collaborate with anyone on that side of things, he’s at the very, very top of the list. He’s so good. Just incredibly, incredibly, not just gifted, but talented in a way that you know — in a fashion that you know is the output of hundreds of thousands of hours of refinement and practice, if that makes sense.
Harley Finkelstein: That’s cool.
Tim Ferriss: Shoe Dog. It’s on the list. We’ll swap, since I’ve read Open, but have not read Shoe Dog. Harley, is there anything else that you would like to say, any closing comments, anything at all that you would like to add before we wrap up for this round one?
Harley Finkelstein: Probably the full circle comment is that you and I are sitting here midway through the year, a little past that, 2020, one of the things that — we talked about mentorship on this, in the last hour or so, we’ve talked about people in our lives that have helped us and certainly we talked a lot about entrepreneurship. But one of the biggest things for us in our story is having, not really mentors, not necessarily advisors, but people along for the ride that are fans, are supporters, are catalysts for those days that are challenging. And I remember this particular moment, it was in 2015, it was May 2015. We were at the New York Stock Exchange. We were about to take the company public. And I remember looking down and our families were there and you were there as well at the Stock Exchange.
And I remember thinking what an incredible journey it’s been, not just for Shopify, but also to have people like you, Tim, in our lives helping to support us, helping to lift us up when we thought things were a little bit tough and we weren’t necessarily sure what direction to go into. I don’t know if there’s a term for that, maybe it’s just friend, maybe it’s just supporter, but for those listening, you find these people throughout your own journeys, whether personal or professional, that in some ways will change the trajectory of where you’re going. There may not be a term for it, it may not be obvious where you’re going to meet them, like a green room at some tech conference, like Rails Conf in your case. But these are the people that in the story that are super valuable to have.
And I want to say, just for a moment of gushiness or of emotion for a second, that it’s been an incredible honor and privilege to have you as one of our supporters the entire time and certainly in the last decade or so, Tim. It’s been amazing for us and anyone out there, find your group of supporters, however you can. It changes everything. And it enables you to do things that you couldn’t otherwise do, whether it’s, “I’m going to give away $10,000 for a competition.” And that supporter says, “No, that’s stupid. Give away $100,000.” They push you to be better. They see a better version of yourself than you see. And I think those are the people that they help make magic. And you certainly have been that for us. And I’m just very grateful for that.
Tim Ferriss: Thank you so much, Harley. I wish you could see my smile right now. I’ve had such an incredible journey with you and Tobi and the gang. And I view you as a brother, 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.
Harley Finkelstein: I like that term. That’s a good one. Companion on the path. That’s a nice one.
Tim Ferriss: Yeah. That’s how I look at it. And I think 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.
Harley Finkelstein: Yeah. Totally.
Tim Ferriss: At least with the sentiment, with which I intended. And —
Harley Finkelstein: But those people, those companions, in many ways, they are the difference makers. They are the ones that, it’s not even those that raise the bar for you, although they certainly play that role too. But the way that 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 green room and try to find them. But I am suggesting that when you do find them, that you marinate that relationship, that you work on it, that you continuously leverage and connect with them to say, “Hey, I’m thinking about this other thing.”
I mean, like I said earlier, as early as this morning, I pinged 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 advice. And it’s just this amazing thing that you can find. And 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 freaking powerful.
Tim Ferriss: 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, Tobi, and others as exemplars of the opposite, which is leading with a 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?
Harley Finkelstein: Totally. It does. And actually, because we are playing the long game. We want Shopify to be 100-year company and we ourselves want to be doing this for a very, very long time. And if you use a lens of very long-term perspective, whether it’s 100 years or 50 years, you begin to reinterpret and reevaluate how you engage with people. You begin to think about things in totally different terms, even if I’m not going to get an immediate ROI next year, who cares? If I can help someone now who eventually may or may not want to help me back later on, that’s good enough.
But I absolutely agree with you, this connotation or this idea that you have to dog eat dog is the way to win, I don’t think that’s the case. In fact, I would actually say entrepreneurship is the opposite of that. The cool part about entrepreneurship is the more entrepreneurs that you help, the more people that want to help you, it creates this incredible virtuous cycle. And that’s where things get really — I mean, that’s the flywheel, that’s where stuff gets really good.
Tim Ferriss: Yeah, absolutely. And people can check out Finite and Infinite Games by Carse as also a good meditation on a lot of this stuff. Harley, always so much fun. This was, at the very least, a good excuse just to catch up and jam and talk for a couple of hours. And people can find you on Twitter @HarleyF, Instagram, @harley, website harleyf.com, obviously shopify.com and we’ll link to the Build a Business and past videos of the trip to Fiji and Gatsby Castle and all of this craziness.
Harley Finkelstein: Oh, yeah. I forgot about Gatsby, that was a fun one.
Tim Ferriss: Yeah, which people were getting a real kick out of.
Harley Finkelstein: That’s awesome. That’s really cool. Timbo, thank you for this. I really enjoyed catching up as well. And hopefully for your listeners, they got some value from this, but this was really fun.
Tim Ferriss: Absolutely. And I hope we are hanging out 50 years hence, I’ll keep eating my veggies and fasting on occasion to try to keep me standing for that long. But it’s really fun to have companions on the path. So thank you for being one.
Harley Finkelstein: Thanks, Tim.
Tim Ferriss: And to everybody listening, we will have show notes as always, links to everything that we have discussed at tim.blog/podcast. Just search Harley, and it will pop right up. And until next time, thank you for listening.
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