#359: Tobi Lütke — From Snowboard Shop to Billion-Dollar Company

"Feedback is a gift." — Tobi Lütke Tobi Lütke (@tobi https://twitter.com/tobi/) is the founder and Chief Executive Officer of Shopify https://www.shopify.com/?ref=4hww. In 2004, Tobi began building software to launch an online snowboard store called Snowdevil. It quickly became obvious that the software was more valuable than the snowboards, so Tobi and his founding team launched the Shopify platform in 2006. He has served as CEO since 2008 at the company's headquarters in Ottawa, Canada. Tobi is an active advocate for computer literacy and education, and serves as a board member of Canada Learning Code https://www.canadalearningcode.ca/, an organization working to give all Canadians access to digital skills. In 2014, Tobi was named The Globe and Mail's CEO of the Year https://www.theglobeandmail.com/report-on-business/rob-magazine/meet-our-ceo-of-the-year/article21734931/. He served as Chair of the Digital Industries Table https://www.ic.gc.ca/eic/site/098.nsf/eng/00009.html, an advisory board commissioned by the federal government to provide recommendations on how to turn Canada into a digital leader. Please enjoy! Click here for the show notes for this episode. https://tim.blog/2019/02/07/tobi-lutke-shopify/?utm_source=podcast&utm_medium=podcast&utm_campaign=podcast-description This podcast is brought to you by Peloton https://www.onepeloton.com/, which has become a staple of my daily routine. I picked up this bike after seeing the success of my friend Kevin Rose, and I've been enjoying it more than I ever imagined. Peloton is an indoor cycling bike that brings live studio classes right to your home. No worrying about fitting classes into your busy schedule or making it to a studio with a crazy commute. New classes are added every day, and this includes options led by elite NYC instructors in your own living room. You can even live stream studio classes taught by the world's best instructors, or find your favorite class on demand. Peloton https://www.onepeloton.com/ is offering listeners to this show a special offer. Visit onepeloton.com https://www.onepeloton.com/ and enter the code TIM at checkout to receive $100 off accessories with your Peloton bike purchase. This is a great way to get in your workouts, or an incredible gift. Again, that's onepeloton.com https://www.onepeloton.com/ and enter the code TIM. This episode is also brought to you by LegalZoom https://www.legalzoom.com/. I've used this service for many of my businesses, as have quite a few of the icons on this podcast, such as Automattic CEO Matt Mullenweg of WordPress fame. LegalZoom https://www.legalzoom.com/ is a reliable resource that more than a million people have already trusted for everything from setting up wills, proper trademark searches, forming LLCs, setting up non-profits, or finding simple cease-and-desist letter templates. LegalZoom https://www.legalzoom.com/ is not a law firm, but it does have a network of independent attorneys available in most states who can give you advice on the best way to get started, provide contract reviews, and otherwise help you run your business with complete transparency and up-front pricing. Check out LegalZoom.com and enter promo code TIM at checkout today https://www.legalzoom.com/ for special savings and see how the fine folks there can make life easier for you and your business. *** If you enjoy the podcast, would you please consider leaving a short review on Apple Podcasts https://podcasts.apple.com/us/podcast/the-tim-ferriss-show/id863897795?mt=2/iTunes? 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Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:01Tim Ferriss?

  At this altitude, I can run flat out for a half mile before my hands start shaking.

• 0:06Speaker 01

  Can I ask you a personal question?

• 0:08Speaker 02

  Now would seem an appropriate time.

• 0:12Speaker 01

  I'm a cybernetic organism, living tissue over metal endoskeleton.

• 0:24Tim Ferriss?

  This episode is brought to you by Peloton, which I've been using probably for about a year now. Peloton is a cutting-edge indoor cycling bike that brings live studio classes right into your home. You can also do on-demand, which is what I do, we'll come back to that. So you don't have to worry about fitting classes into a busy schedule or making it to a studio or gym with a hectic or unpredictable commute. I, for instance, have a Peloton bike right in my master bedroom at home, and it's one of the first things I do many mornings. I wake up, I meditate for a bit, then I knock out a short 20-minute ride in my undies, hard to do that at the gym, take a shower, and I'm in higher gear for the rest of the day. It's really convenient and has become something that I look forward to. So you have a lot of options. For one, if you like, you can ride live with thousands of other riders across the country

• 1:09Tim Ferriss?

  on an interactive leaderboard to keep you motivated. There are also up to 14 new classes added every day with more than 8,000 classes on-demand, and you can pick based on length, 45 minutes, 20 minutes, whatever, music, hip-hop, rock and roll, or say, low-impact versus high-intensity or interval. You can pick the class structure and style that works for you. And in my case, I quite like Matt Wilpers, and I tend to do on-demand and listen to a lot of and watch many of the same classes over and over, but I'm kind of promiscuous and also enjoy classes from a lot of the other instructors. They have, Peloton, an amazing roster of incredible instructors in New York City with a whole range of styles and personalities, so you can find what you're in the mood for. You also get real-time metrics that you can use to track your performance over time,

• 1:54Tim Ferriss?

  and that will help, I would say catalyze you to beat your personal best. Now, that all sounds good, right? Gamification, yada, yada, yada. I didn't think that it would work for me or in any way incentivize me, but they really 100% hit the nail on the head. I was very, very excited. Impressed with how motivating it was and it worked tremendously to keep me pushing, which quite honestly takes a fair amount. I can get quite lazy, particularly with anything that edges on endurance, which is kind of more than five reps of anything for me. So, check it out. Discover this cutting-edge indoor cycling bike that brings a studio experience right to your home. Peloton is offering listeners of this podcast a limited

• 2:34Tim Ferriss?

  time offer. Go to onepeloton.com, that's O-N-E, peloton, P-E-L-O-T-O-N, dot com, and enter the code TIM, all caps, at checkout and get $100 off of accessories with your Peloton bike purchase. So, get a great workout at home anytime you want. Check it out. Go to onepeloton.com and use the code TIM to get started.

• 3:01Tim Ferriss?

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• 3:45Tim Ferriss?

  because LegalZoom isn't a law firm. So, they won't be running the clock up and spinning circles just to raise your bill. Instead, they just ask you to pay one low upfront price for whatever it is that you're looking to get, à la carte style. So, visit LegalZoom.com and check out their business section for all of their services. And if you want special savings, that's the terminology in the copy that they suggest. I don't know what the special savings is, folks, but it's titillating. If you want special savings, enter promo code TIM, T-I-M, at checkout. Capital T, lowercase i-M. Again, take a peek, LegalZoom.com, and enter promo code TIM.

• 4:29Tim Ferriss?

  Hello, boys and girls, ladies and germs. This is Tim Ferriss and welcome to another episode of the Tim Ferriss Show, where it is my job each and every episode to deconstruct a world-class performer from any number of different domains: business, sports, entertainment, military, and so on. And today's guest, who will perhaps debate that he himself is world-class, but I will not allow it, is Toby Lutka, who is the founder and chief executive officer of Shopify, CEO that is, of Shopify. In 2004, Toby began building software to launch an online snowboard store called Snowdevil. It quickly became obvious that the software was more valuable than the snowboards, so Toby and his founding team launched the Shopify platform in 2006.

• 5:12Tim Ferriss?

  He has served as CEO since 2008 at the company headquarters in the metropolitan epicenter of tech, Ottawa, Canada. It's a fantastic place. I've spent time there. Beaver Tales, also incredible. Toby is an active advocate for computer literacy and education and serves as a board member of Canada Learning Code, all caps, C L C, Canada Learning Code, an organization working to give all Canadians access to digital skills. In 2014, Toby was named the Globe and Mail's CEO of the Year. He served as Chair of the Digital Industries Table, an advisory board commissioned by the federal government to provide recommendations on how to turn Canada into a digital leader. And that report was published, that is, of the table, in September 2018.

• 5:56Tim Ferriss?

  Toby, welcome to the show.

• 5:58Speaker 03

  Thanks so much for having me.

• 5:59Tim Ferriss?

  And I feel like this is a long time coming. We go way, way back, and we'll get to that. But I thought we could start with your penchant related to optimization. So I want to do a quick fact-check here. So this is something I came across in The New York Times. It doesn't surprise me.

• 6:20Tim Ferriss?

  But here's how it goes. "I also have a weird obsession with optimizing things." This is supposedly a quote of yours. "Even when I was walking to elementary school, I counted the number of steps on different routes so I could figure out which one was shortest." And I'll just finish this up. So, dot, dot, dot, I'll just connect some things. "If I had to do something once, that's fine. If I had to do it twice, I'm kind of annoyed. And if I had to do it three times, I'm going to try to automate it." Did you count steps?

• 6:47Speaker 03

  I did. It's a little bit difficult, isn't it? It's one of those situations, you know, like where I think I was together with my mom, my sister, and my sister was complaining about me trying to optimize something. I think we were talking about going for a walk and I'm like, well, you know, if a place we're starting from is the same as a destination, why don't we just not go? And my mom merely said, you realize you did this from when you were like four, I was, and told me the story and it's kind of sort of unfortunately probably tells people way too much about me. So I don't know why this made it into the New York Times. I'm actually kind of unhappy about this right now, but here we are.

• 7:27Tim Ferriss?

  And here we are. And the the optimization or the looking for efficiency, is that something that your either of your parents has or does that seem to kind of come out of left field?

• 7:40Speaker 03

  I think, I don't know. It's probably one of those unexplained kind of quirks which then after probably many, many years where it's annoying everyone around me suddenly starts becoming useful, right? Like after, you know, because, you know, especially as a programmer, it's been wonderful, right? It's, you know, I love these old machines where, you know, can understand every chip that's in the machine. You can kind of figure out what's what, try to, you know, make a video game in 90s was really, really hard. And so those are the kind of things which really, really attracted me.

• 8:13Tim Ferriss?

  And so just to give people a snapshot of where things are now, and we're going to certainly continue with this retrospective rewinding of the clock, but how big is Shopify at the moment? What are some of the numbers?

• 8:25Speaker 03

  So, as I said, Shopify started in 2000, 2004 and became sort of, we released it in 2006, which again, that's almost like 100 internet years ago, right? It's been a long time. And the company now is a public company. It's about four and a half thousand people work at Shopify. We have offices in largely across Canada, but also in, you know, Berlin and in Australia and so on and all sorts of other places. We have about, I don't know what the newest official number is, I think it's called mobile 700,000 customers and all around the world, 175 countries and so on, so on, so on.

• 9:13Tim Ferriss?

  It's become this, by almost any metric, fantastic success. I was mentioning when we were having lunch before this that I was unpacking some boxes that I had not yet unpacked from my move from San Francisco to Austin. And I found the coin from the initial public offering. And it really made me smile because I remember when we first met Shopify had, what would you say?

• 9:41Speaker 03

  Fifteen people.

• 9:42Tim Ferriss?

  Fifteen people. And that was, was that 2008 or 2009?

• 9:47Speaker 03

  2008.

• 9:48Tim Ferriss?

  It's 2008. And could you tell what you remember of that first meeting? Where did we first meet?

• 9:56Speaker 03

  We did, we met at a conference called RubyConf, right? It might have been RailsConf.

• 10:04Tim Ferriss?

  RailsConf.

• 10:05Speaker 03

  RailsConf, that sounds right. Ruby and Rails being the technology Shopify has been programmed in. And you were invited as a keynote speaker. I think you did an interview with David.

• 10:20Tim Ferriss?

  That's right. David Hanameyer Hansen.

• 10:22Speaker 03

  Exactly. So I think we talked in the green room, like, hey, I love everything about your book, but the worst part about it is you keep talking about using Yahoo Stores for your supplement business and you really should have used Shopify. And you know, what can I do to convince you of, I wasn't that direct, I was probably really shy.

• 10:43Tim Ferriss?

  But the timing was perfect also because I was in the process of doing the final editing for the revised edition of the Four Hour Work Week. And I had been polling my readers through social media and the blog and so on, which had, at that time, you had the blog already, at that point, had millions of readers, and asking for suggestions for updates for the tools and resources. And Shopify was the most consistent recommendation for e-commerce platform. And then I go to this conference, we meet in the speaker's room, effectively.

• 11:26Tim Ferriss?

  Let's say 15 or so employees and that was the beginning of our exchanges and then collaboration, which which we'll get into, but it on one hand seems like a previous lifetime and on another hand just does not seem that long ago.

• 11:43Speaker 03

  It doesn't, doesn't.

• 11:44Tim Ferriss?

  And I have to say for people who perhaps wonder this, does money change people? I have to say it's been so, I didn't expect you to change and you didn't and it's really refreshing and I don't know if I've said this publicly, but Shopify is one of those companies where everyone I've ever been involved with has been just such a genuinely good person. It's an example of when the good guys have have won in a way and it's it's it just makes me so happy that you guys have had the outcomes that you've had, so.

• 12:23Speaker 03

  Thank you so much for your time.

• 12:24Tim Ferriss?

  Yeah, I just want to want to start there. It's really just, it gives me so much joy to think about and let's get back to your odd behavior as a kid. So it's, this is, this is from a separate piece and this isn't going to be all quotes, but some of these are just so fantastic, I can't, I can't not mention. This is from Globe and Mail and this, this I think speaks to a superpower of yours that may have caused problems in the beginning and I recall reading a quote and I'm going to butcher it, but Francis Ford Coppola, the director, incredible legendary filmmaker, had said, you know, you receive lifetime achievement awards for the things that would have gotten you fired in the beginning.

• 13:08Speaker 03

  That's fantastic.

• 13:12Tim Ferriss?

  Yeah, so here's the quote, and this is the writer, "From an early age, Lutka had what he calls authority problems. In schools in Koblenz, Germany, he preferred to deconstruct the questions teachers gave him rather than deliver the expected answers." And I was like, yep, that sounds right. "He took shortcuts determining the minimum number of hours he needed to spend in a particular class and still pass so that he could spend most of his time with his computer." One of the patterns that I have observed with you over the years that I think is so, so valuable and so simultaneously.

• 13:50Tim Ferriss?

  Important but undervalued or under discussed is not just asking the question in front of you, but dissecting it to determine if it's the right question. So could you elaborate a bit on that or think of any examples that could serve as a launching off point or even maybe start with why you do this?

• 14:14Speaker 03

  Yeah, well, this is already going into interesting places, isn't it?

• 14:20Tim Ferriss?

  Yeah.

• 14:20Speaker 03

  Like, okay, we are talking about my authority problem and my obsession with optimization. So where do we go from here? Here's one thing, which is here's what the authority problem thing has morphed into. And I think this is exactly the pivot point from which you went from problematic to very useful. And that is, I have a serious problem just of accepting autotaxy. Like, here's how things are done. Just kind of, that doesn't grab me in any particular way. And so what I've determined for myself is, I really want to understand the situation

• 15:02Speaker 03

  and the various pressures acting on the situation that I might get myself into. So you were taking us back with your little coin that you found, which is one of those artifacts the New York Stock Exchange gives you when you take a company public. And so we got to do this together. Before that date, when you actually ring the bell, you, at least traditionally, like companies like Spotify and Slack are now doing the direct listing, which I think is really, really healthy for that particular industry. But before that, you went, you worked with bankers, you built this prospectus, and then when you go on a roadshow and all these kind of things, you spend a grueling, like, talk

• 15:44Speaker 03

  about, I don't want to do a thing two times, like, three times. I had to give the same presentation 103 times in eight days. It's absolutely, it was a complete haze.

• 15:57Tim Ferriss?

  Toby's version of hell.

• 15:59Speaker 03

  It was my. Which is funny because like my business partner Harley is like the opposite of me and loved it. So it's good to have these people around who can.

• 16:10Tim Ferriss?

  Side note, so Harley, Harley probably the person I've heard most described as a force of nature. That phrase applied to Harley.

• 16:19Speaker 03

  Exactly, which I'm decidedly not. So Harley loved it. I wanted to automate it all the way through. But just I'm taking us back there because I think this is a good example of this kind of thinking.

• 16:36Speaker 03

  One thing I did very early in the process of actually taking the company public was to

• 16:42Speaker 03

  not just understand like how could Shopify become like a good public company. But there was this sort of obvious agency problem that exists on the investment banker side, right? And so I spent a good couple of months

• 16:58Speaker 03

  talking to people figuring out what kind of things happen in the performance review of investment bankers. Like how do they make their money? How do they make their bonuses? How do they, you know, how do, how do they string together career? What's good, what's bad, you know? If they get a lot of these kind of fees, is that good for them or is that neutral? If they, you know, so because this is, this is, I would like to come to a conclusion. Like and often this is the same conclusion that Orthodoxy would have just sent me to myself. Because I want, I want to say, okay, I'm gonna do these following things. Because I from first principle argued that this is the right thing to do.

• 17:40Speaker 03

  And I think this more often than not actually leads to very interesting

• 17:46Speaker 03

  insights where you can say, okay, because I understand what's at play here. I can disagree with someone's suggestion and I can maybe improve something slightly. And I think in an interesting way, Shopify is a very long exercise in doing this over and over and over again. Rather than saying, okay, well. The internet needs online stores. They are super important. Entrepreneurship is one of the biggest economic opportunities. Online retail is one of the biggest entrepreneurial opportunities of our lifetime. It's like 1.9 trillion dollar industry now. It's going to be 4 trillion soon.

• 18:24Speaker 03

  Online stores need to be something that people can create. Okay, cool. But do people really care about online stores? They care about selling, right? They care about becoming successful entrepreneurs. They care about reaching for independence and the success of that. So which pretty quickly sent us into a direction saying, okay, well, we do the online store thing, but let's actually build the software that actually supports people in the activity of reaching for independence. And because of this, it became something else and success came through that.

• 18:58Tim Ferriss?

  This also, in a way, connects some dots from earlier today when we were chatting about a mutual friend, Seth Godin.

• 19:06Speaker 03

  Yeah.

• 19:07Tim Ferriss?

  And Seth and I, not too long ago, had this conversation where he gave the example of, which was borrowed from an example he had read, but he elaborated on it, which was, no one wants a quarter inch drill bit, they want a quarter inch hole. And it's like, no, but they don't really want a quarter inch hole, they want a shelf. They don't really want a shelf, they want a place to put their books and so on and so forth.

• 19:27Speaker 03

  Yeah.

• 19:29Tim Ferriss?

  So that you don't mistake the current characteristics of a temporary solution as the ultimate objective.

• 19:36Speaker 03

  Because the world has sorted itself into solutions based on a world that's long gone, in a way. Like, why, I mean, just looking back at my industry, like, why was there a online store industry and a point-of-sale system industry? And all these eBay power seller tools? Like, each of those instances, someone has a product and wants to sell it through whatever channel. Like, do you want to go to like three, four, five different vendors to get software to participate in all these channels? No, you just want to do it, right? And so I think it's really worth going for life and just saying, well, hold on a second.

• 20:20Speaker 03

  Like, what are people actually trying to accomplish? What is the actual problem here? I think the most impressive story along those lines that I've ever sort of come across is the, are you familiar with Malcolm McLean's story around the invention of a shipping container?

• 20:36Tim Ferriss?

  I'm not, but I've had a book about shipping containers recommended to me multiple times.

• 20:41Speaker 03

  Probably.

• 20:41Tim Ferriss?

  The box.

• 20:42Speaker 03

  Yeah.

• 20:42Tim Ferriss?

  What was the name, the person's name you said?

• 20:44Speaker 03

  His name was Malcolm McLean. He's, he's, he's one of those entrepreneurs who would absolutely be on your podcast if he would be alive right now, right? Because spent the first money out of college on buying a truck, started a trucking company.

• 21:00Speaker 03

  And tried to get things shipped across the country or even to Europe and realized like we can make the most efficient trucking system. Or the, the train guys have the most efficient trains and the boat guys have ships all over the world. But getting something through multiple stations is impossible. Like you have to unload everything, load in next. So he ended up just buying a bunch of tankers from the US Navy, uh, which had surplus tankers at the end of World War Two. And just, just came up with this idea of putting a shipping container together, but you can put things in the factory in Maine and then bring ship them all the way to Berlin. And the moment he did that, the, the cost of, um, sending like a unit of goods went from, I think, six dollars to 16 cents.

• 21:43Tim Ferriss?

  It's incredible.

• 21:44Speaker 03

  We all live in Malcolm's world because the shipping container has been hugely influential, um, in history. It's like a lot of people talk about free trade agreements and globalization. In reality, it's globalization happens the moment a shipping container opens in a country and it's, it's a fascinating, like rather underexposed story. But what's so cool about this is, um, the reason why he pulled this off is because, um, again, the, the Vanderbilts and the train guys really loved their trains. And, and the boat guys loved boats. And he was the only person who just cared about moving things. He wanted to solve a problem of moving things in the world and then you come to better solutions and we need more of that kind of thing.

• 22:28Tim Ferriss?

  Yeah. The, uh, the versatility, I don't want to get too taken off track, but the shipping container, when I was, the, the brilliance of the modular design. And the ability to take a single container and move it across different means of transport.

• 22:45Tim Ferriss?

  Is an endlessly fascinating topic and a lot of folks also don't realize the sort of genius of the design of shipping containers and the considerations of the dimensions and the ability to cool or control temperature. Then the entire aftermarket use of shipping containers also, which is how I came into it. I kind of backed into it, looking at different types of design and construction. That book was called The Box.

• 23:12Speaker 03

  Yes.

• 23:12Tim Ferriss?

  The Box. So since we're talking about it, might as well, might as well just hit on, on something I was going to ask about anyway, which is, which is books. So you're a, I would say a voracious, but very selective consumer of information. And there's a lot of garbage out there. You mentioned The Box. There's another book, and I think it might have been in Harley's office where I first saw it at Shopify, but High Output Management by Andy Grove.

• 23:44Speaker 03

  That's one of the best books ever.

• 23:46Tim Ferriss?

  One of the best books ever. So I want to, and then another one that I have listed here is Drive by Daniel Pink. I'm not sure if you want to comment on that, but could you mention a few books that you have found particularly helpful? And maybe start with High Output Management and why that is a good book?

• 24:07Speaker 03

  So I'll take you back to the early days. I started at Shopify as, you know, hey, I only want to do the technology. I'm a programmer by trade, right? So this is my world. And I wanted to treat business as a black box for the first couple of years. And then for various reasons, I was sort of thrust into also having to take over the business side of Shopify. Around that time, actually, we met. And I did a poll with people I knew for two books to read.

• 24:39Tim Ferriss?

  So business folks.

• 24:40Speaker 03

  Exactly. So because I I was at this point, I was knee deep in Martin Fowler and and Ken Beck and all these kind of luminaries of the of the programming world, but I had no idea about business. And so um the two books I read, um which is funny because it tells you how good that selection process was because I still think was a probably they would rank in the top five books I've ever read. Um and I had a completely wrong view about how good business books were afterwards. Where High Output Management by Andy Grove and Influence by um

• 25:15Tim Ferriss?

  Keltini.

• 25:16Speaker 03

  Keltini, exactly. Um. So that was a very fortuitous two first books to read.

• 25:22Tim Ferriss?

  You got off to a good start.

• 25:24Speaker 03

  Yeah. Um. So so Andy's book is unapologetically uh almost a how to man manual that kind of just deconstructs the world of business into its into first principles. It's like, here's what matters. Here's how to think about it. No one needs a degree. There's there's a little bit of circumstantial, contextual understanding that you just have to have. But basically, it basically at the end of the day, making a business is an engineering exercise. And which is brilliant for me because that's like that actually connected that that made the whole thing about becoming a CEO significantly less scary to me because you know, engineering, I understand.

• 26:08Speaker 03

  And then Influence was just the most mind bending book you can imagine because it essentially told told you all the ways humans are flawed and influenceable and um how um yes, computers are predictable and you can deal with it, but then once once you make things for people, you need to go into storytelling and uh you know, framing matters, which were also news to me. I spent my teens with computers, not with people.

• 26:35Speaker 03

  So um I I I came as a like my my wife would you know, would dine out on this topic and just probably make fun of me for hours. But like she she she always says, I'm an I am an immigrant to a human condition. So was to send me off to a good start. I just want to say, well, um, uh, various reader, various, various, that's how you say that. Um, uh, like I'm dyslexic. I actually read very slowly. Um, I sort of overcome dyslexia, but like I, I, I read books very slowly. I think I, it's actually an advantage. Frankly, I have very high recollection, but

• 27:18Speaker 03

  because of this, I have to be very selective on the, on the books I read. So I'm not one of those a hundred books a year kind of people.

• 27:26Tim Ferriss?

  Yeah. How do you, how do you choose books now? Or maybe as an example, like the box, why did that come on your radar? How did that make the cut?

• 27:34Speaker 03

  Um, the box came because I, I usually have a topic and then just dive, right? Like I, I, I dive into it. Like in this, in this case, I was like, hey, I'm running Shopify. Shopify causes, um, you know, billions, like tens of billions of dollars of commerce activity. And most of this is going to go through a logistics network that I don't understand. And I feel my job as a CEO is to have the most full stack understanding of every component in the, that's at all related, um, which is frankly, given that we're working here in world trade is almost the entire human condition. Um, so it's an endless source of interesting deep dives into topics. But in this case, I was more

• 28:17Speaker 03

  about the logistics world. Like it's, it's, it's a fascinating world because it's been built for millennia. And, um, um, you know, like the, the Silk Road, um, has still impact on the way the world economy works today. And then stitching these things together is absolutely fascinating. But, um, uh, just even in the sort of first, okay, let me, let me, let me start digging. It became pretty clear that the, that there was a History before the shipping container and history after the shipping container. And if in these situations, when there's a specific date where everything changes, like when the industrial revolution or something, another example of that. What I tend to like doing is I like to find the players, like the people who had a lot

• 29:01Speaker 03

  of input on this kind of thing, or just at least who had the front row seat, and then read their biographies, because they don't tend to try to sell you anything other than that this person played an important role, but they tend to be the most credible witnesses to the actual outside events without so much bias towards convincing you that it was good or bad. And so in this particular case, it was very easy. There was actually a perfectly good book about exactly the guy who came up with it. And so it was an obvious choice.

• 29:30Tim Ferriss?

  What other, actually, before we get to subjects and more books, because this may bridge over to something that I did not know. I feel like I should have known this, and it makes perfect sense, but I did not know this. So this is, I suppose, one of your problem domains. We can discuss what that means. When you became CEO, and I have a question about that also, but this is a quote from a media piece, and I could try to paraphrase it, but it'll take a lot longer. So you, as part of, here's the piece, as part of his self-directed crash course, he decided to fly to Silicon Valley. Now, I'm going to pause here for a second because people listening might think, of

• 30:15Tim Ferriss?

  course, you go to Silicon Valley to learn from fantastic entrepreneurs and so on. But it's, it takes a different turn here, which I think is really indicative of how you're thinking, how you apply very structured thinking to things. Back to the piece. He set up meetings with venture capitalists and listened to their questions about Shopify's attrition rates and conversion rates and funnel, in parentheses, the various means by which a company attracts the attention and secures the commitment of new customers. It's a long way to say that. He had no idea what they were talking about, but he wrote down the terms. Then he went back to the hostel he was staying in and looked, that also tells you something, hostel he was staying in and looked up everything on Wikipedia. He would then read up on how to calculate contribution margin ratio.

• 30:58Tim Ferriss?

  And the amount by which sales exceed variable production costs, then go to Shopify's database and get the numbers. Oh, he'd think that's an interesting way to look at the business. Then at the next meeting, he was able to answer one more question. This is this is a really clever way to go about.

• 31:12Speaker 03

  Thank you.

• 31:13Tim Ferriss?

  Getting up.

• 31:13Speaker 03

  Fix that time.

• 31:14Tim Ferriss?

  I mean, you're learning by observing the questions and then defining the terms.

• 31:18Speaker 03

  See, this is why I love podcasts. My favorite thing in the world is like books are like definitely rank up there, but it's there's one thing which is better, which is being a fly on a wall than two experts talk amongst each other, right? Which is one of those situations that was almost impossible to line up as an outsider and now suddenly is completely democratized for the wonderful invention of podcasting. But back then, and before that, I sometimes managed to do it via finding a chat room or forum where experts talk amongst each other. It's something I was always seeking in this case. So when I was trying

• 32:00Speaker 03

  to learn about some technology, like some esoteric 3D rendering algorithms that I was found interesting, I used to try to find like where people talk about optimizing these things. And then I just don't understand anything that they're talking about, but then I chip away at it and I would come into the knowledge. And so I tried to replicate this and talking to venture capitalists ended up being sort of the way I figured out how to potentially do it. Because again, I had no background in business. I had no idea how this all worked. I had and I had to do it fast because 2008 Shopify wasn't doing well, right? Like it was very, very tough to keep the company alive.

• 32:44Tim Ferriss?

  So let's, let's, this is maybe a good opportunity to explain to people why you took over as CEO. Just the circumstances.

• 32:53Speaker 03

  The circumstance was simple and probably fairly common. It's I had a co-founder of Snowdevil, which was a snowboard store. And we did the like I did the technology, he did ran the store and did a million other.

• 33:08Speaker 03

  Things like find us an office at some point. But as the company pivoted much more to being a software company and started growing and acquire more and more people at some point, like it was just a different situation. And so he sort of came to me and said, decided that he wanted to transition out. And that really, you know, I mean, that was very surprising because again, I really wanted to treat business as a black box. I thought business just, I mean, it was a programmer. We don't like business.

• 33:45Tim Ferriss?

  Yeah, that's, I was gonna, I was gonna say treating it as a black box is a very diplomatic way to say it as a programmer.

• 33:50Speaker 03

  Yeah, yeah, yeah. Yeah, like, I mean, I just didn't want to like become the pointy head. Boston with the bad comic, right? So I, so this is the situation. It just arose and I, I actually looked for a CEO for a long time. I, I met with a lot of people who got came recommended as potential CEO replacements. And it was one of my early investors, the, the, actually the only investor, frankly,

• 34:24Speaker 03

  who at some point took me aside and said, Toby, you will never find anyone who will care about Shopify as much as you do. And so you should just give this a go. And that was pretty scary advice. But I liked the challenge. I mean, why do we entrepreneurs do this thing? It's like, why, why do we even build companies? It's, it's such a silly idea, right? Like, think about how irrational this is. This is not my quote, but like, someone said, like, you, you spend a hundred hours a week avoiding working forty hours a week for someone else.

• 35:04Speaker 03

  It kind of makes no sense, right? Like, and with a very especially tech, like such a minor chance of actually getting any kind of returns on it. And so you don't do this for, for, for, uh, at least certainly, well, I can't, I can only speak for myself. I certainly did not do this for monetary reasons. Um, reason why I did it is because I thought it sounded amazing not having to answer to anyone, you know, back to authority problems. And, um, uh, I, I wanted to make my own sort of technology decisions and these kind of things. Um, and I want to see what I can do. I, I want to challenge myself. And I said, like, this is the right time in my life. I was, uh, 24 when I started. Um, this is the right time of my life to give this a go.

• 35:47Speaker 03

  Uh, I will learn a ton. Like, there's no way this could be a failure on a personal level other than in the way that, you know, maybe people lose money. I mean, but, but real failure is a very, was a very real thing, but, um, I knew I would learn a lot. And so that I reconnected with them and said, okay, there's another challenge to become the business side of a business as well. And, um, uh, I'm going to learn a lot again. And so, um, I traveled to Silicon Valley. I, it's funny because I, I found this hostel close to, uh, Center Road, where all of these were back then. Um, and, uh, I bought a bike on Craigslist and, and, and just biked to all these things.

• 36:31Speaker 03

  And they must, you know, they, they even see, like, if you look at Center Road, it's not made for bikes.

• 36:37Tim Ferriss?

  It's not made for bikes.

• 36:39Speaker 03

  And, uh, biking into these like gleaming palaces of capitalism.

• 36:45Tim Ferriss?

  I just have to imagine they're like, yeah, some guy's coming in from Ottawa, Canada. Ottawa, Canada? They're like, wait, is that him on the bike?

• 36:51Speaker 03

  This is exactly the situation. You're, you're, you're just, you're just adding to the, the picture that, that, that's perfectly accurate. And, um, um, uh, yeah, so I, I talked with them, I learned a lot. Um, I, I thought they found this. Somehow I was endearing in some way because I actually did keep contact with a lot of them. They didn't actually run me out of their offices, which is also speaks to Silicon Valley. You know, it's an amazing place where you can take meetings with people who will give you their time and advice. And I puzzled it out, right? Like I figured it out. It turns out I needed to learn a lot about certain terms and so on, but yeah.

• 37:33Tim Ferriss?

  Figured it out.

• 37:33Speaker 03

  Figured it out.

• 37:34Tim Ferriss?

  And I'd love to talk for, well, first, first an observation, which is how much, how much fun it was for me and also instructive to meet you when I met you, right? That's really, that is quite a transitionary period in which to meet Toby. So it's, it's been really, really fantastic to watch as things have evolved over time.

• 38:07Tim Ferriss?

  That now that said, part of what makes it interesting is the good decisions, but also the challenges and maybe some of the bad decisions. Can you talk to, in any order you like, some of the, some of the good decisions that you made and some of the bad decisions that you made when, after taking on the role of CEO?

• 38:27Speaker 03

  Yeah, it would be good to have some sort of obvious examples here, but I mean, it's almost every good decision starts somehow bad first, right? It's, there have been, like, we've made almost every mistake in the book, but we are also the kind of company that wants to, in a way. You know, like we, it's been so important to me to build a company that is kind of, that is unafraid of experimentation and where failure, like within Shopify, we don't even, we sort of, I think we succeeded in this. We eliminated the talk of a term failure, like we, we, we name, we call it the successful discovery of something that did not work because I think it really changes people's disposition to it.

• 39:12Speaker 03

  So what did we do wrong? Like we did.

• 39:17Tim Ferriss?

  Well, I was just gonna say, I mean, I don't want to interrupt your answer, but if I think that what you just said could also take us in a pretty interesting direction. If you want to buy some time to think about the failures.

• 39:28Speaker 03

  Let me buy some time.

• 39:29Tim Ferriss?

  Not failures, failures in quotation marks. So there are a number of things that seem paradoxical that I don't think are paradoxical in practice. Maybe they are, but I want you to comment on them. And I just have to find the right quote here. Well, I'll give you the first part. So the first part is a quote of yours, I believe. "Your work here needs to make an impact like a crater." Right? So it's not just good work. It's not excellent. It's massive cosmic impact. It needs to be visible from outer space. And so people are encouraged to take risks.

• 40:08Speaker 03

  Yes.

• 40:09Tim Ferriss?

  Now, at the same time, another quote here. Toby Shannon, right? All right. So this is on, you know it's coming. This is on receiving feedback from Toby. "Be prepared to be crushed," says Shopify's Vice President of Revenue Toby Shannon. "If you can't be crushed, you don't make it on the executive team. You need thick skin." It's not that Toby shouts or treats people meanly. He's simply direct, unfiltered. When he looks at the fruits of someone's labor, he says what he thinks, even if what he thinks is this is shit. Okay.

• 40:49Tim Ferriss?

  So how do you combine these two things successfully? One of the things I love about you is that it is, you don't get the sugar-coated kid glove version of Toby's thought. You get Toby's thought. So how do you encourage risks when the feedback you receive at the end might be, that was total shit. You can do better.

• 41:14Speaker 03

  Yep. Now, I want to register that that quote came up in 2015, and you know, since then, I have learned that I should translate something like, "This is shit," into, "Is this really the best way we can do this?"

• 41:36Speaker 03

  But it's um, uh, I mean, it's the same thing in a different form, really. Here, I, here's something I've always liked, Wikipedia, right? Like there's a, I hope I get the name right. There's a, a specific editor from the early days of Wikipedia, who I think was called, he had a handle called Kronker. And he declared something called Kronker's Rules, which said that he wanted everyone to edit his pages, just to make them better. And he didn't want people to apologize for it and or try to politically like give him credit or something.

• 42:14Speaker 03

  He said, I'm gonna take a hundred percent um, uh, responsibility for my own mental state. Like I, like you cannot make me unhappy by just giving me feedback in some way. Um, so just give me the raw feedback without all the like shit sandwich around.

• 42:32Speaker 03

  I love that. I, I, I just, I would like to run my team on Kronker's Rules because I think it's just, there's, there's so much time spent. Like first you have to talk about the weather and then, you know, like. You need to say nice sweater, that's a really nice sweater. Exactly. So you have to find something and then ideally address some very productive character traits. Then talk about the thing you wanna talk about and then figure out some way of afterwards talking about something highly positive again. So, you know, that's, that's the sort of standard formula. And um, I can do it, but I don't think that um, the highest performing teams in the world should spend time doing this uh, to each other. I think there's a level of progression that comes um, if you're part of one of the teams.

• 43:16Speaker 03

  And again, like we are one of the bigger technology companies in the world, certainly, I think we're fastest growing SaaS company um, um, on the market. And uh, so, you know, it's not like, I wanna compare too much to sports because sports is, it's sports is sports, but. This is like a big game, right? Like we need to be very good at what we're doing. Otherwise, you cannot build Shopify. And so I think these things are in the way. And so, yes, I want people to be impactful. Like, again, if a hard object collides with a soft object, then suddenly, like, there's no crater to prove it, right? And so I want people to take their sort of mental state in their own hands and just say, okay,

• 44:01Speaker 03

  I'm gonna learn how to be intrinsically reminded that I'm good at what I'm doing and not have to rely on other people constantly telling me.

• 44:09Tim Ferriss?

  Do you help? Does Shopify have any type of training or resources or cultural rules that are explicit that help to facilitate that type of awareness? Because there are people who meditate for 10 years with that objective and never quite get there. And you can hire the talent. You can already find the people. Like, you could go out and you could hire Jocko Willink, right? To run your HR department. I'm kidding. And he would give them all a copy of Extrino Ownership and be like, oh, here we go. But then there are people who come in who might be exceptional performers, but very sensitive in some way. I've run into that quite a bit.

• 44:51Speaker 03

  Yeah.

• 44:53Tim Ferriss?

  What do you do in a situation like that? Or what are the things that you do or that Shopify does to help people take that ownership of their internal state? Because this is hugely important.

• 45:03Speaker 03

  Yeah, it's hugely important. So one thing that's so neat about Shopify is, again, let's get a little bit back to this Ottawa, Canada thing, right? Clearly, as you said, this is off a beaten track of the startup world. Ended up being a phenomenally good place to build a world-class company, but for reasons that were also not clear to me when I started there.

• 45:29Speaker 03

  A couple of things that happen when you're not in Silicon Valley, right? Or like in the not, let's call it a primary, like, company creation city.

• 45:41Speaker 03

  Tenure gets longer. If I hire someone through this very intricate hiring process that we have, there's sort of an understanding that the chance of us still working together in ten years is actually really high. Right? I mean, it's a commitment from both sides and the company needs to be worth working for for ten years. That's what I work on day in, day out. But because of that, we can have a very different relationship than in a place where the expected tenure is eighteen months. In an eighteen month place, I really have to kind of access every good idea and the productive power of, let's say, an engineer or so immediately. They need to be productive.

• 46:26Tim Ferriss?

  And they need to be really pampered in some cases.

• 46:30Speaker 03

  To even keep them for the eighteen months.

• 46:31Tim Ferriss?

  That's right. If you have Facebook, Google, and then name five other companies who are all pitching the same employees at those five companies.

• 46:39Speaker 03

  Yeah.

• 46:40Tim Ferriss?

  Via headhunters.

• 46:41Speaker 03

  Yeah. And so in a place like this, ends up for better or for worse in a world where people don't actually go having careers at companies anymore because the way to have a career is actually jumping between companies. Your new position is always slightly higher. And so, well, our cities aren't like that. We assume that we have these long-term, tenured relationships and therefore Shopify can invest in the people who are part of Shopify in a completely different way. So we have a big amount of, we probably hired all business coaches in Canada and beyond at this point to be full-time employees of Shopify because we're investing so much in the people.

• 47:24Speaker 03

  We hire people on future high potential and then try to get them there as fast as possible because that actually works for us and that works for people and works for Shopify fantastically well. And so we have a lot of these opportunities because of that to make some slight edits to the normal psyche, right? Like so, feedback is a gift. It's such a simple sentence, but really is not the way most people think about feedback, right? And

• 47:54Tim Ferriss?

  Feedback is a gift.

• 47:55Speaker 03

  Feedback is a gift because it is, it clearly is. It's not, it's not meant to hurt. It's, it's meant to move things forward, right? Like to, to demystify something for you. I want, I want frank feedback from everyone and I, I get it. Although funny enough, I don't know if you know, like you might have a thought about this. I tend to get it from the Germans at Shopify more frequently than anyone else. So, so there might be a cultural component in here too.

• 48:23Speaker 03

  So, um, uh, but yeah, so this like, did he say call it crusher of egos or get your ego crushed? That sounds so dramatic.

• 48:33Tim Ferriss?

  Yes, be prepared to be crushed. If you can't be crushed, you don't make it on the executive team.

• 48:36Speaker 03

  Yeah, I, I, I would say that might be a little.

• 48:40Tim Ferriss?

  Or learn, learn how not to feel crushed.

• 48:42Speaker 03

  Yes. So, so I mean, this is the executive team, which is directly my team of the people who have the highest requirements of. And we have worked together for the longest. So I think, um, I don't think it's like this or everywhere in Shopify.

• 48:56Tim Ferriss?

  How, so are there particular, hmm, particular books, particular types of training, exercises that are used within Shopify to help people take ownership of their internal state? Or to view feedback as a gift that people listening might be able to use or explore or think about in some way?

• 49:15Speaker 03

  If a company is, they're very, um, I like different companies have different sort of personality trait testing kind of things that they like. Shopify is very partial to a system called Enneagram.

• 49:27Tim Ferriss?

  Enneagram. I just had my first Enneagram typing last week.

• 49:31Speaker 03

  And you are a eight?

• 49:33Tim Ferriss?

  I appear to be a loyal skeptic six.

• 49:39Speaker 03

  Oh, wow. Interesting.

• 49:41Tim Ferriss?

  Yeah.

• 49:42Speaker 03

  There you go.

• 49:42Tim Ferriss?

  Yeah, we could, we could get into it. This is all new to me. This is all new to me, but, but.

• 49:46Speaker 03

  It's interesting, well, but Enneagram, uh, it has been, it has worked very, very well for us. Um, like in, in our internal system, you can actually see the Enneagram of everyone else. And it tells, it tells you like how, like what nuances that means for how to work together, for instance. So that's one, but the other thing, I think why personality tests are interesting is they, it doesn't even matter which one it is. After you kind of do one, it already kind of teaches you like, hey, wait, wait a second. The way I'm wired is different from the people around me.

• 50:18Tim Ferriss?

  Yeah.

• 50:18Speaker 03

  And I think this is so fruitful of a discovery, especially early in your career. Right. Because again, a lot of the people we hire, like average age of Shopify is thirty, twenty nine, I think. So we get to people very early in their career. And because what the thing that we want to accomplish, and this is really the goal of all of internal programs, is we want to take people from a find out what parts of,

• 50:48Speaker 03

  what kind of areas they have a fixed mindset on and try to get people to become, to acquire growth mindset, right? Just think of their intelligence as something that can be trained. Think of their skill as a programmer, not as something static. And when someone comes and tells you that there's something you could have done better, that's not someone finding out that you're not as good as you thought. That's actually a teacher appearing, right? And once people acquire this growth mindset on at least a number of different trades, usually they arrive to, like they make it very, very far and they can have these like ten years of a career in one year on the work clock.

• 51:30Speaker 03

  And it's a wonderful kind of thing when it happens.

• 51:34Tim Ferriss?

  How would you suggest that people acquire a growth mindset? Because there are books, I don't know if great, I haven't read Angela Duckworth's book, Great, it's been recommended a number of times. But there are a number of books that talk about the importance of growth, fostering growth versus fixed mindset in child rearing. And you shouldn't say, you're so smart. You should say, you worked really hard and did a good job and so forth.

• 52:05Speaker 03

  Yeah.

• 52:05Tim Ferriss?

  Because inevitably, if they have what's perceived to be a failure or make mistakes, it's then not indicative of them being stupid, but rather

• 52:15Tim Ferriss?

  and something related to effort and or chance that they can play a part in resolving or improving. Right. But if we're talking about Let's just say there's, there are any number of people certainly listen to the podcast and like, you know what, like, I'm sure I have a fixed mindset somewhere, but I don't, I don't, I don't know if it's a blind spot. I don't know where, how I would spot it. And then how do I fix it? What would your thoughts be?

• 52:39Speaker 03

  Um, I think that it's a really, really good question. I wish I had a better answer. I, I do find that Carol Dweck's original book called Mindset is probably still the best source.

• 52:50Tim Ferriss?

  That's D W E C K, right?

• 52:53Speaker 03

  Yeah.

• 52:54Tim Ferriss?

  Yeah, Carol Dweck. Yeah, that was also, uh, we were talking about Josh Waitzkin during lunch, also a book that he's quite a fan of.

• 53:01Speaker 03

  Yeah, I'm a big fan of the book. It's, it, it at least talks you through a theory. And what I've observed is even the very, very high, um, super successful executives, um, who come to Shopify and or have worked at Shopify for a very long time. And they, they end up reading the book. Um, and they said, you know what? I was actually fixed mindset on all, on all these, like, these three things. And it's like, it really irks me now. I, I, it's, it's just really funny the way how, um, it, it just sort of wakes you up to this, uh, to, to this reality that we can all have it. It's, it's not something you can over completely overcome. Um, but it's something that just

• 53:40Speaker 03

  having the awareness, um, is, is really powerful. And also if you're, if, if you have direct reports in a company, um, even if that book does nothing for you, it will allow you to be a much better lead to those people because it's like just priming you to detect, uh, fixed mindset talk in other people and pointing it out is hugely beneficial.

• 54:02Tim Ferriss?

  So when I want to, uh, note an observation that may or may not be true, but it, it seems to me that the discussion of fixed and growth mindset goes, it pairs quite well with Enneagram also. Enneagram, by the way, I was introduced to by Drew of Dropbox.

• 54:18Speaker 03

  Oh, yeah.

• 54:19Tim Ferriss?

  And I was always skeptical and I still am somewhat skeptical of certain aspects of Enneagram, which I think actually means nine pointed. Uh, so there are nine different types. Uh, then there's a lot of discussion of, uh, through different books and experts about Enneagram. But like you said, in your commentary about Enneagram, it's not necessarily the specifics of the sort of business acceptable horoscope that you get. It's the fact that you begin to look at relating to other people and your weaknesses and/or fixed mindsets differently. Right? And so I found it very useful.

• 55:03Tim Ferriss?

  I had my, I'm going to have, well, my girlfriend did her typing. And I'm going to have all of my employees do their typing also, just so they think with an awareness about interactions through that lens, even if the exact content may be, you know, 50% kind of hand wavy, if that makes sense.

• 55:23Speaker 03

  Yeah, because here's why all these things matter. I once read that, I in particular believe in hell, but I like this definition of it. Hell is meeting the best version that you could have become at the end of your life.

• 55:37Tim Ferriss?

  Yeah.

• 55:38Speaker 03

  And so I think that one of the really, really fun things about, you know, an experience like an entrepreneurial journey, like with a company, the careers we have, the books we read, like if they end up being pointed in sort of a direction that allows us to minimize the difference between that person we will meet and the person we are at that point of time, I think that's time well spent. And there's some key, I think, events in one's life that have to go through it. Like at some point, hopefully, you realize that the people around you are very different, that you have some unexplained traits in you, which some of them being,

• 56:22Speaker 03

  becoming big strengths and some of them are weaknesses. And you double down on your strengths and you try to work around your weaknesses. And by the way, later in life, it might actually flip which ones is which, which is, gets really weird. But that's another one of those kind of things. The sort of awakening to a growth mindset is another one of those life events, I think. And so.

• 56:46Speaker 03

  These events matter because what you're building eventually is like some kind of path that allows you to wake up smarter every day. Then if you do, if you get there, really, really powerful things happen. Suddenly, you know, jumping into like a completely new job that you have no qualification for, suddenly doesn't sound scary anymore. I mean, it probably still does a little bit, but the challenge and the thrill of it, of like, this sounds real, I could fail, I now have to, I have to grow to make this work, actually become hugely motivating.

• 57:25Speaker 03

  And I think that one of the most amazing things that anyone can go through and can do in their lives is to, like, is a variation on the theme of going on a journey, doing hard things surrounded by friends, right? Company building is one of those things, often travel is another one, sports are really good at these kind of things.

• 57:52Speaker 03

  I would love Jocko's opinion on if it was like that.

• 57:56Tim Ferriss?

  Oh, I think you would definitely say that.

• 57:58Speaker 03

  So, you know, variations on this theme is what you want to prepare for.

• 58:03Tim Ferriss?

  I want to come back to something you mentioned earlier that I think is very, very relevant here. So you talked about, I'm gonna try to tie a few different things together. You talked about taking risks and looking for opportunities for massive impact. You also talked about how you have looked at certain opportunities or transitions as opportunities for learning and that you've made a lot of mistakes, but it seems to me that you've even in some ways optimized for learning. And I just want to highlight for, for folks listening and also just to remind myself that this is something that comes up quite frequently with people who seem to just step

• 58:47Tim Ferriss?

  up to bat and hit homerun after homerun. If you really dig under the hood, that's not necessarily the case, but for instance, people who are in any number of different fields, whether it's Scott Adams and Dilbert. Or some of the investors I deeply respect, like Marc Andreessen, who's been on the podcast. They talk about combining, rather than trying to be, say, the top 1% in the NBA, which is very hard to do and very attribute dependent. You could be, say, top 10% or even top 25% in things that are rarely combined, right? It could be computer science and law. It could be Warren Buffett in value investing and public speaking.

• 59:30Tim Ferriss?

  He says the best investment he ever made was in a Dale Carnegie public speaking course, because it magnifies everything else that you do. And so there's the combining of skill sets that are rarely combined. And as Scott has also written about quite extensively, and I agree with that if, if, and I'm paraphrasing here, so I might be mixing and matching a little. But if you optimize for learning new skills and developing new relationships that transcend any one given project, it's really difficult to fail completely. Right? And so you end up accumulating these skills and relationships

• 1:00:10Tim Ferriss?

  that then help for you to combine these different disciplines in unique ways. So that I just want to mention, because it's, it's, it's tempting and debilitating to think that you have to be the absolute best, top 1% in X. And when you, when you really look at people, whether it's all the, all the various billionaires and magazine covers or what have you, that's not necessarily the case.

• 1:00:35Speaker 03

  No.

• 1:00:36Tim Ferriss?

  Yeah.

• 1:00:36Speaker 03

  I, so I could not agree more with you. And I, it's interesting, because I almost have two phases to my life in this regard, right? Because I really was trying to become, I don't know. I don't know if I was trying to become the best programmer in the world, but I certainly was making a bit for it. You know, like, my life was completely revolved around writing code, understanding more of it, and, and then just being very good at it. I was going for mastery anyways. And then this. Situation that happened there again, I had to like pause that world. And have to go in like into business and I ended up really, really liking so many aspects of it.

• 1:01:17Speaker 03

  I I I really pivoted to I would like to from from someone who is gonna try to get I I would like to understand hundred percent of a field. To I wanna as quickly as possible, understand eighty percent of every field, right? And that's I like it way better on this side and I'm internally thankful for having realized this at at some point. Because it's um it is uh it actually doesn't take that long to um Emmy, you wrote an entire book on this. I'm obviously not trying to convince you on this, but it it doesn't take long to to to understand the first eighty percent of of of any number of fields, right? And um but of course, you can't understand the eighty percent of every field, that's that's too many.

• 1:02:01Speaker 03

  So you'll you'll follow your interests pretty automatically and and then you find out exactly this uh what what you just said. And this is something, you know, sort of it's it's worth looking into the Shopify universe. There um the people were really successful, other people who usually have some multiple skill sets and combine them into some kind of new product. It's like in sort of an obvious example is like boosted boards, right? Like hey, he's like electric engineers um who also like skateboarding. Let's combine those two things by putting a battery into the skateboard. And so it's really, really, really hard to be the best in the world at a single discipline. But as soon as you start overlaying like three different interests, um you make Pokémon inspired jewelry or something.

• 1:02:46Speaker 03

  You can make the best Pokémon inspired jewelry in the world um um uh pretty quickly, right? And so

• 1:02:53Tim Ferriss?

  The the the speed with which you came up with that makes me think that that's a store on Shopify somewhere.

• 1:02:58Speaker 03

  Absolutely.

• 1:03:02Tim Ferriss?

  Because you're I mean, you're in a great position to see, I mean. Hundreds of thousands of these examples.

• 1:03:08Speaker 03

  We see millions of success stories and and and attempts at success stories, right? This is honestly the the most interesting part of Shopify is is really um the the the like we see this, right? We like, let's actually zoom out for a second here on on my entrepreneurship topic because it's it's really dear to me. But it's also at a state that a lot of people don't really quite appreciate. Entrepreneurship is in big crisis right now. It's it's a complete counter narrative to what most people most people think. But um right now, new company formation is at the lowest points ever been. Gen X was is um started a lot less companies, a lot fewer companies than its parents.

• 1:03:50Speaker 03

  And millennials are lower yet, so it's the least entrepreneurial generation so far.

• 1:03:56Speaker 03

  And um the the numbers are going like companies that are um, you know, like all all numbers are downwards.

• 1:04:03Tim Ferriss?

  Is that measured by LLC formation, entity formation?

• 1:04:06Speaker 03

  Just general companies that are of all classes in the United States over time. Once you look at the graphs, they all they all just they're looking like a tank. It's especially since two thousand and five, sort of two thousand and six. The beginning, very beginning financial crisis has suddenly fell off a cliff.

• 1:04:23Speaker 03

  So why is that?

• 1:04:25Tim Ferriss?

  Tell me Toby.

• 1:04:26Speaker 03

  Right, I I well, I wish I wish I would know. It's like, I know some contributing factors, like one thing is we just don't need too many copies of everything anymore. Like back in the day, you probably visited, you lived in a smaller community, you visited a big one. You saw, hey, here's like, what, like certain kind of hardware store, you know, some kind of, you know, business you've never seen before. You'd say, hey, I might be able to do that back home and that's a new company, right? Now everything's franchised and like centralized and it's it's a lot harder to do these kind of businesses. But the same thing is going on on internet as well, right? The internet is, as much as it can be a democratizing force, it really benefits centralization.

• 1:05:11Speaker 03

  You know, we have one social network, it's one one search engine and so on. So um. It is harder to start businesses. And like you you you kind of have to clock in in the top center of of a field or at least an intersection of a field of multiple fields to even partake in entrepreneurship. And that's, I think that's not good. I I mean, if you would give me like, hey, here's like two versions of the world. Choose one, one in which entrepreneurship is common and easy and straightforward. And and one where it isn't like, like, I mean, who does who takes the one where it isn't? Where it isn't easy, right?

• 1:05:50Tim Ferriss?

  So how would you make it? How would you make it easier, whether in the U.S. or maybe not Canada specific? It could be, but is there is there anything that you would do to increase the number of entrepreneurs? And why is that important? Is it important?

• 1:06:05Speaker 03

  Yeah, I mean, that's a good question. I I think should be studied. I mean, like, one, one thing, if you if you look at this completely from an economics perspective, like, we we, if you if you think that we need to provide employment to people, you should want, like, a couple mega companies are not going to employ everyone, right? I think everyone understands this. It's, we need millions of ten, twenty people companies, SMBs. That's almost everyone is employed by small businesses. If you look at the actual numbers. So with small business going away, that that that's that's definitely a force into the opposite direction. So how would you do it?

• 1:06:50Speaker 03

  I mean, one thing is, this is actually a real problem in the United States, but it's actually a problem everywhere is licensing. Like, it it's a crazy situation that I can get a laptop and start fifteen billion dollar Shopify and not need to ask no one, but if I want to become a hairdresser, I need to get a license for it, right? And I need to go for like, like, and there's quotas in many places and you can't because for all these reasons. So so that's kind of one of those things that probably people have to have a look at. But the other one is just friction. Like, how how difficult is it? Like, how many things do you have to understand to start an online business? Like, you you built, like, a supplement business back in the day. What are all the things you had to learn?

• 1:07:31Tim Ferriss?

  Well, I remember, I think this was even before that, when I was taking a stab at a few businesses, all of which

• 1:07:40Tim Ferriss?

  Self-immolated, but just setting up a merchant account, I remember.

• 1:07:45Speaker 03

  Right.

• 1:07:45Tim Ferriss?

  Back in the day was a huge, it was a complex and hugely involved task.

• 1:07:52Speaker 03

  I had to post a $30,000 bond to get a merchant account when I started Snow Devil.

• 1:07:58Tim Ferriss?

  Yeah.

• 1:07:58Speaker 03

  That was all the capital I had, so.

• 1:08:02Tim Ferriss?

  It's wild.

• 1:08:03Speaker 03

  So, but those kind of points of friction are everywhere. Like, I mean, this is, I don't want to make this mad, but like Shopify is not the solution to this problem because it's a much more global and bigger problem. But the retail world is one of the most accessible parts of entrepreneurship. And that's really all Shopify is, like, try to take the learning curve of partaking in like entrepreneurship, building online businesses, and make it as flat as possible so as many people can succeed, right? That's what we've been working on for the last, what is it, 14 years now?

• 1:08:39Tim Ferriss?

  I think this might be a good place to chat about the build a business competition.

• 1:08:44Speaker 03

  Oh, yes.

• 1:08:45Tim Ferriss?

  The build a business competition, we've been talking about just smoothing the path or removing impediments to entrepreneurship, but you also have incentives. Incentives are also important. What is the build a business competition?

• 1:09:00Speaker 03

  Let's go back to where it's come from because this is, I mean, so relevant to, I think, two of us, but certainly to me. I don't know, it's relevant to you, but you were involved.

• 1:09:14Speaker 03

  So this was 2009. So at this point Shopify was completely running on fumes. It's like my, we were completely, it just,

• 1:09:26Speaker 03

  all sorts of things didn't work. Like you asked me earlier, like things that didn't work, like the company kind of didn't work, right? It wasn't, like, I had the numbers and people were selling things and it was valuable to them, but there was no real business being built around it. And it kind of all just didn't function. My father-in-law was gracious enough to give me a cheque every week for the running payroll. So at that stage, and he said he would do that for a certain time. And by the end of it, we've kind of have to figure out what to have to do. At this point, we were talking and the reason why, again, we see the world in a similar way. You wrote for Workweek, but what attracted me in this book is like what you were talking about.

• 1:10:10Speaker 03

  You know, just building like a business and then actually doing other things. Well, like I was seeing people doing this on Shopify, but was like, this is an underexplored form of, you know, what you can do online. Like people, people should know about this, that this is what some people do. And we should obviously tell people that that's what people do on Shopify and Shopify is good for this kind of thing. So we had this conversation, I was at my college, I was actually on a boat when we had this conversation. And we're like, you know, how can we overcome this built-in fear of failure that everyone's running around with?

• 1:10:51Speaker 03

  Everyone, like so many people, I come to me, come to you and say, one day I'm going to start my own business. It's like, okay, what about today? You know, what's wrong with today? And there's always all these kind of reasons. And I think our working theory was we just should, we need to test this by really incentivizing people. And to which I said, we should like, I don't know, we should give away like a MacBook Pro. And then you did what you always did in our phone calls. It's like, like Toby, first of all, that's way too nerdy and only you care about MacBook Pros. And then second, if you want anyone to notice, you need to go like a hundred X that in terms of price or something like this.

• 1:11:35Speaker 03

  Which is probably easier to say on your side.

• 1:11:39Tim Ferriss?

  I also remember exactly where I was, by the way. I was in Glen Park, walking down, I think it's Diamond Street, past Oshita. I remember the exact block I was on when we were having this conversation.

• 1:11:50Speaker 03

  Yeah, it's funny. Yeah, like sometimes these things are just branding in your mind because I think we both realized, like we were egging each other on to make something big. And what ended up, what we ended up doing is said, okay, you're gonna take the last hundred thousand dollars in the bank and just put it up as a competition and say whoever is gonna build the biggest business like from starting now in the next six months is gonna just get the check. Which is at this point, I said, this is either going to work and then we'll make the money during the competition to then give to people.

• 1:12:33Speaker 03

  Or companies bankrupt anyways, in which case, you know, I'll deal with that in some other way. But we did, and I think through some contact of you, I think you introduced me to Laura, the New York Times ended up talking about it. Because it was like surprising. It's like tiny startup in Canada, putting up something that's beyond like every business plan and competition in terms of price money, right? It was a pretty stunning amount.

• 1:13:01Tim Ferriss?

  Yeah, biggest ever.

• 1:13:03Speaker 03

  It was a huge success. Exactly. You were like super confident that it would be a big success from the beginning. I thank you for this because I wasn't. I was like, oh my God.

• 1:13:15Tim Ferriss?

  And it's, it's, it's been really, it's been really awesome to watch also year after year as it has grown and evolved. So I mean, you could give some examples, but from the beginnings, right, which are, we're not entirely sure. I mean, on some level, you know where this hundred thousand is going to come from, but this is sort of an existential bet in a way. But like you said, it's like there, there are other kind of inherent issues that if we don't do it, it's not clear what the picture is going to look like. And then you flash forward. And you're doing these build a business competitions.

• 1:13:58Tim Ferriss?

  It's like a high end reality show in the sense that you have, you know, the mansion from The Great Gatsby with DiCaprio. People are flying all over the world and you have Tony Robbins coming in to mentor the finalists and so on.

• 1:14:16Speaker 03

  We took everyone to Fiji to his place.

• 1:14:21Tim Ferriss?

  Just it's been so much fun to watch and you guys have done a fantastic job of executing. And it's ended up coming full circle also as I'm considering with the audience that I have, what could I do potentially competition wise? You guys have taken the ball, run with it and have done this so many years now. I'm like, hey, which lawyers do you guys use?

• 1:14:50Tim Ferriss?

  Turns out, by the way, anyone who's thinking about doing something like this, I mean, you have the prize money, but then you have the putting together of a competition of this complexity, which is no joke.

• 1:15:01Speaker 03

  No joke. Every state, even every province in Canada has completely different laws for this. Everyone will come and ask, hey, is this a game of chance here or is this a game of skill? Which is actually an interesting question for entrepreneurs. Because the intellectually honest answer is like chance. I mean, I try to never get confused about this. Like Shopify is enormously successful, but it's like 99% chance, right? Like you can predict all this kind of things which happen to transpire, which led to success. So, but of course, when you're talking to the lawyers, you have to say this is a game of skill. Absolutely, I have a bit of skill involved.

• 1:15:43Speaker 03

  Yeah, so we launched this in 2010 and we had an amazing winner event with Dodo Case, right? It was so cool.

• 1:15:51Tim Ferriss?

  Can you tell people a little bit about that?

• 1:15:53Speaker 03

  Patrick and Craig, two brilliant entrepreneurs from San Francisco who

• 1:16:00Speaker 03

  Then what they what they did, I think this was around the launch of iPad. And so they realized these iPads need cases, just like the phones. And so they got together with some traditional book binders and made some so mold skin looking like beautiful, like it was really just wood and whatever mold skin is, a case for iPads. And I think they gave sort of flyers to everyone waiting in line around the Apple store before iPad got launched. So they people wrote about it and they were one of the competitors in the competition. They won it and fantastic story. There's a later picture of President Obama

• 1:16:45Speaker 03

  with his Dodo case, which of course they used very successfully in everyone one of the marketing campaigns. And just I think actually like which goes back to sort of the thing that really excites me about the fact that come from all these kind of things, not just was this an entrepreneurial success story for them and they got a hundred thousand dollar check in there and they also quadrupled or even beyond the amount of professional book binders in the San Francisco Bay region again, like this was something like this is an area which had a lot of book binding talent and then that was an industry and that's not an industry anymore because it's just not done manually anymore.

• 1:17:28Speaker 03

  But they got people out of retirement to come back making these iPad cases and then just a little industry exists there. And I think this is just the stories which just I find so, so great.

• 1:17:39Tim Ferriss?

  So let's, let's talk about, we don't have to get into all the specifics of, of a ton of them, but I was very curious from the first competition to see what can people do, like what can people actually do?

• 1:17:52Speaker 03

  In six months, right? Six, eight months, it's nothing.

• 1:17:54Tim Ferriss?

  I mean, but some of these people are creating multimillion dollar businesses

• 1:17:58Speaker 03

  Unbelievable.

• 1:17:58Tim Ferriss?

  from ground zero.

• 1:18:00Speaker 03

  Yes.

• 1:18:01Tim Ferriss?

  And it's, it's been really inspiring to watch and inspiring not just because of the size, but also the variety. That having been said.

• 1:18:12Tim Ferriss?

  One of the things I look forward to every year when you guys are running the build a business competitions is what patterns will emerge because you begin to spot and this is much like I feel like with my audience from say the four hour work week or the podcast, but just the millions of entrepreneurs who allow me to pattern recognize because I just have the 30,000 foot view on my audience, show me things that are coming, right? It's like the William Gibson in Neuromancer said the future is already here, it's just not evenly distributed. So you see these patterns that are sort of this like smoke signal in the distance and then five years later, it's everywhere. And with Shopify, for instance,

• 1:18:55Tim Ferriss?

  I remember the first year that a number of the category winners, because there are different categories, right? So it's not, it's not all or nothing in term, at this point in the competition. There are different, what would you call it, industries or product categories, which, which gives more people a chance to win. And it's like, wow, okay. So I'm making this number up, but it's like three out of the six used Kickstarter. That's interesting. And looking at the different tools and different approaches, different tactics and strategies that seem to be used with, with great efficacy each year is also something that I have really looked forward to.

• 1:19:40Speaker 03

  And this goes beyond the tools into the approach, I think. And this is actually where I feel like I learned the most from, from, from the entrepreneurs, because these are really the best who are coming. Like, I mean, it's actually, we had first time entrepreneurs win categories, but like, they always had some kind of fantastic insight that they're kind of adding to this exploration about how to build companies in this digital age. So, so even the Kickstarter folks, one thing, the question I always had is like, was Kickstarter itself valuable? Or was it that they had to put a certain video on their website, which

• 1:20:22Speaker 03

  Founders of a company had to explain why this product needed to exist, right? It it seems like such a like, why does not every product in the world have some have have the inventor declare why they felt this thing needed to be created? Like, why is why can I only get that from the people who happen to go on Kickstarter, right?

• 1:20:41Tim Ferriss?

  Yeah.

• 1:20:41Speaker 03

  And um, the most of them ended up figuring out approaches which are really about storytelling. Like, what what's the story? Like, the Dodo Case story is a story of revitalization of a craft, right? Which people connected with. The the the the beautiful object that came out of it um was completely imbued by this story. Um, and and if if if uh, then then I was walking around with my Dodo Case, like uh, someone would talk about it. I would talk about, hey, what's how this was handmade by real book binders? Because I owned a part of that story. And um, that's that's that's really the great thing. The the the really great thing is that um, things that are powerful and work have actually not changed in the internet age. Like, we we are all kind of, I mean, our ancestors are the ones who were the storytellers,

• 1:21:26Speaker 03

  or at least the people who listened the most to the stories. This is how language developed, you know, like we are we are storytelling creatures. And it's um, it just is rediscovering this medium after medium is is something that is really, really fascinating.

• 1:21:38Tim Ferriss?

  And if you if you look back to the the two books you mentioned, right? If you're looking at Influence, or you're looking at Andy Grove's book, also not snapshot in time dependent on the technology of right now.

• 1:21:55Speaker 03

  Right.

• 1:21:55Tim Ferriss?

  These are principles. And uh, you know, I've I've I've often thought about Kickstarter also and and other platforms like it as a talent assessment for some of the basic competencies that one will need in the company they would then subsequently build. Right? It's like, if you cannot sell your product in a video and then marshal resources and try to garner PR, however, however you take your approach to raise a re in in potentially nominal sum of money for a first manufacturing run, like, how could you ever have the confidence then that you would be able to proceed and build something large over an extended period of time?

• 1:22:39Tim Ferriss?

  Like, it's a it's a it's an audition in a sense. And um, so then it brings up all sorts of other questions. Just getting back to the very first thing, or one of the first things I asked you about, like. Questioning the question, it's like, is it a survivorship bias? Is it that there are more people attempting things? And therefore they can kind of stress test and then run with the things that work. And that is why you have this higher percentage peering in say a Shopify build a business competition. In any case, it's, it's been, it's been such a fun ride. And thanks for having me as part of it.

• 1:23:19Speaker 03

  Well, you kind of started. You shouldn't, like, you shouldn't downplay your, your, your input on the whole thing, so.

• 1:23:27Tim Ferriss?

  Yeah, it's, and I wanted to also, before I forget, and since I think other people listening might find it of interest, mention a book that's kind of going to segue over to something that may or may not bear fruit, we'll see. But the, the book that I would recommend, all right, bear with me, guys, this is going to get very Tim Ferriss ADHD for a second. But you mentioned dyslexia. Do you not have any issues with real time review of code as you're writing it?

• 1:23:57Speaker 03

  No.

• 1:23:58Tim Ferriss?

  Okay, that's interesting.

• 1:23:59Speaker 03

  None.

• 1:24:00Tim Ferriss?

  Yeah, okay, that's just for another time. I was just like, sort of neurologically and optically, that's very interesting to me.

• 1:24:06Speaker 03

  Interesting. It's a fascinating question, but no, I don't.

• 1:24:09Tim Ferriss?

  Okay, all right, so the, the, and I just had that come to mind because I'm going to recommend a book, but it's, it's a short book by a reasonably recently deceased Jesuit priest who is also trained as a therapist named Anthony DeMello. The book is called Awareness and the subtitle is The Perils and Opportunities of Reality. But it's a collection of effectively transcribed talks that were given by Anthony. It was recommended by a guest on this podcast, Peter Maluk, who's in finance. And I, I decided to pick it up because he said it, every time he reads it and he rereads it more than any other book, it gives him an extensive sense of peace.

• 1:24:52Tim Ferriss?

  And I was like, that's an interesting, that is not the phrase or explanation that I would expect.

• 1:24:59Speaker 03

  It's a hell of a way to sell a book.

• 1:25:01Tim Ferriss?

  Yeah, and I picked it up and Awareness, The Perils and Opportunities of Reality, I think will.

• 1:25:10Tim Ferriss?

  You might just find Strikes A Court. It's a very easy read and for me, it did give me this extended sort of afterglow effect of inner peace for about two weeks. And I've decided that I'm probably going to reread it less than a month after having finished it. And it is, it's proven very valuable for me, even though I do have a meditation practice, to reinforce through the prefrontal cortex, the value of owning your internal state and be choosing to be or develop the responsiveness as opposed to reactivity.

• 1:25:50Tim Ferriss?

  And this, on a macro level, makes me think of comfort, discomfort, and how humans relate to that. Something that came up in doing research for this was the concept of, and then I may be, I may be barking up the wrong tree here, but we'll see where it goes, the next box and what the box is, not in the shipping container sense. Could you talk about what I'm referring to?

• 1:26:20Speaker 03

  Yeah. It's a term from a talk I gave. I was invited to like a local event and they needed me to do a keynote and I don't tend to do these kind of things a lot. But I kind of wanted, there was something, they just asked me to share something. And so I said, well, personal growth is something that I'm thinking a lot about and feel like I was going through. So I decided to like, just sort of explain it the way I see it without really going deep into the like current zeitgeist thinking about it. And so this is, this is sort of what I explained.

• 1:27:07Speaker 03

  You know, when you back in high school, I remember being back in high school and I remember that, you know, there was cool kids and uncool kids and, you know, we probably were two different sides of that kind of divide. I was, I was the uncool kid.

• 1:27:23Tim Ferriss?

  I was the Dungeons and Dragons nerd kid, so I actually got my ass kicked up until about sixth grade and then a growth spurt and then I was, I was just an angry, rageful vigilante. But up until sixth grade, I was definitely in the, in the nerd camp.

• 1:27:39Speaker 03

  Alright, so, and again, I don't know why we keep talking about me as a kid because it's not that interesting, but it seems to keep coming up. This is already going to tell you way too much about me as a kid. At some point, I decided, okay, I want to analyze why some kids are cool and why I'm not. And what I came back with was the, the cool kids all had Air Jordans.

• 1:28:07Speaker 03

  So, so I wanted them too. And of course, at some point, I got them and it totally didn't make a difference. But, but the reason why this is valuable is the high school is sort of, it's, it's, it's a universe. It's kind of a box and it's hard to get in it because it feels very uncomfortable. You don't understand it. You don't understand the social network, the influences. And then you're trying to kind of make sense of it, right? In, in your own way. And, and it actually becomes reasonably comfortable then after you sort of explain it to yourself. Now, it's a small box, narrow, and probably your understanding of it is wrong, like clearly like mine was about how I could join the cool kids, right? At some

• 1:28:49Speaker 03

  point, hopefully, what happens is you, you, you find a crack somewhere in the narrow box you're in and you go into the outer box where this box you just came from is like a tiny parcel in the corner. Like it's a much bigger place, maybe, maybe college or so or work life. But again, it feels super uncomfortable. You arrive in that new box, not understanding physics, not understanding the situation, what's expected of you. It's all ambiguous. You have to reinvent everything. Even the things you figured out before are no longer true and you notice this at sort of an internal level. And the trick is go to at some point, figure out, figure it all out and then comes the dangerous part because it's now comfortable again.

• 1:29:35Speaker 03

  And so what you have to do though is you have to go and find the crack and go into the next box around this, where suddenly all your college life and all these kind of things just are a small box in a corner somewhere and suddenly the world's much bigger and you need to learn more and understand more and so on. I find, I've met luckily at various times in my life, these people who clearly occupied a much larger box and they're just sort of bent down to me to talk to me. Because they could just somehow, like you said this one thing, and what they said back to you was so clearly right, but you could never have understood yourself based on this vantage point you had, right? And they were usually the way how you then entered a larger box and so on.

• 1:30:18Tim Ferriss?

  Can you think of any, or are you willing to give any examples of?

• 1:30:22Speaker 03

  Yeah.

• 1:30:23Tim Ferriss?

  An exchange like that?

• 1:30:25Speaker 03

  I had, it's a recurring thing, it still happens to me to this day. I mean, the specific case I was thinking of back in the day is, I started, I left school at the 10th grade, I started my apprenticeship as a computer programmer, which is a thing you can do in Germany. And I spent a good deal of time on computers, understood them, could do programming and so on. But there was a guy who, by the name of Jürgen Saar, who was sort of my designated mentor in this apprenticeship program. And he was one of those people who not just, like I could ask any question, you would have a perfectly, like you could write it down what he said back, you know, it's like he just, everything came back fully formed.

• 1:31:09Tim Ferriss?

  Sam Harris type.

• 1:31:10Speaker 03

  Yeah, exactly. And, but then also he just created, like, he was just an incredible mentor to me because he created these, almost these scenarios for me, right? Like he, you know, he would do my code reviews and so on, but also he would sign us up to drive to some customer, which I and him were writing some software for, and then he would just find an excuse for not being able to go and just let me go myself. And I was like 17, 18 years old, right? I had just got my driver's license.

• 1:31:37Tim Ferriss?

  I'm just trying to imagine, having spent a lot of time with you.

• 1:31:41Speaker 03

  I had to, I had to get 400 D-Mark, this was before Euros, it's like 200 Euros, to buy a suit from a company. I did not have that money, right? So, going to a customer and installing software.

• 1:31:53Tim Ferriss?

  Now, why, why did he do that?

• 1:31:55Speaker 03

  Because he thought I could do it.

• 1:32:00Speaker 03

  And that was it. Like, it's like he thought, he did think that I would probably not fail. And that was good enough odds for him. And like he also knew the customer well, so he knew that they wouldn't, like, he can pull a stunt like this and they would find it funny. So there was very little personal risk for him. And then, you know, like you do this and I learned a lot and of course my code totally didn't work and I had to use some satellite uplink to get the new version. And like, but I came back and said, hey, in this sort of worldview box thing I was in just yesterday, it's implausible that I would have succeeded doing this thing that I just yesterday did.

• 1:32:43Speaker 03

  So therefore, I think I'm in an uncomfortable new box right now and I have to relook at everything I know and re-categorize everything. And Jürgen kind of just figured out how to get me through a couple of one of those. And so, I don't know if it's a good metaphor for growth. I, I, I, but it's the one that just sort of, kind of, came to my mind when the first time I was supposed to sort of explain this to people. And what I like about it is that it affirms the thing that makes it hard to grow. Because it is the dangerous part of when you feel comfortable in the box you're in. And every one of us has at the family reunion, the one uncle who decided to not traverse into further boxes way too, way too early, right?

• 1:33:28Speaker 03

  They figure they have, the entire world figured out and everything makes sense to them. And of course, everyone else looks at it and says, oh my God, what are they talking about, right?

• 1:33:37Tim Ferriss?

  So I have a few questions about that. This is a topic of comfort zones. Our topic of great interest to me, but also it comes back to awareness as well. For instance, do you know what box you are currently in? And the next box you want to go to, or is it not possible until you have someone bend down? And kind of poke you in the forehead?

• 1:34:03Speaker 03

  I don't think, I don't think you can. I, I'm, I, I know that I'm in, I mean, I, I know I'm always in a box. I actually am. This is personal, like personally, I think I I have figured out the box I'm in and I'm currently not seeing the exit, which makes me uneasy.

• 1:34:20Tim Ferriss?

  Wait, what? I'm sorry, say that one more time, one more time.

• 1:34:22Speaker 03

  I I would say that I understand the box I'm in and I haven't found the exit. And the funny thing is, I've done this so many times that I'm actually really uncomfortable being comfortable. I I really dislike not understanding where my neck, where growth comes from. So I'm I'm I'm a seeker right now.

• 1:34:37Tim Ferriss?

  Are you comfortable sharing what the boxes that you're in that you don't know the exit from?

• 1:34:42Speaker 03

  I mean, it's sort of, I I it's it's nothing, it's nothing terribly profound. It's sort of like, uh, it's it's my life, right? It's um, like, I understand how to be a public company CEO. Um, that's just a crazy sentence that I never, when sixteen year old, we would never have imagined me me uttering. But um, uh, I I I understand the systems of Wall Street and understand the um, um, the the the company that I've built. I understand how to, uh, I think be the best leader I can be for the company. Um, uh, I I've made a lot of progress sort of in my personal life, just sort of, you know, I started working out and, you know, like all these kind of like, just have a meditation practice, you know, all these kind of good things that you've been recommending forever.

• 1:35:24Speaker 03

  Um, and I finally came around to, um, so so so that's that's good, but it's comfortable in a way. Like, I'm I'm I'm seeking right now. I'm trying to poke at this. I I um, I I'm trying new things to figure out how to come break out of it.

• 1:35:38Tim Ferriss?

  How do you choose those things? How do you choose the things that might be the right stress test to find that crack?

• 1:35:45Speaker 03

  Usually, I mean, one, I mean, books are generally good, like far field books are are useful. I'm really interested in sort of uh, in in just psychology right now, because there's a lot of more interesting topics than people think. Um, but I was also challenging myself, you know, like I'm uh, um, I I I'm I'm in a um, in a driver development program for more motors, motor racing, which is super fun.

• 1:36:14Tim Ferriss?

  That sounds amazing.

• 1:36:15Speaker 03

  It's it's like, you know, talk about getting in a car, not thinking about anything for like two hours, three hours. That's it's like.

• 1:36:23Tim Ferriss?

  Yeah, you are highly incentivized not to think about other things.

• 1:36:26Speaker 03

  Yeah, well, exactly, because uh, there's a real repercussions. This is not like the successful discovery of something that did not work. This was a wall.

• 1:36:35Speaker 03

  So, you know, just like, like doing things that, that are just different from, from, from anything else that's fit, like import things from other people's boxes who are presumably in bigger boxes is a way of doing it.

• 1:36:50Tim Ferriss?

  Now, I, I would also love your help to

• 1:36:55Tim Ferriss?

  clarify something, uh, not, not so much for me because I think I know the answer, but maybe for people listening. And that's a distinction. Uh, I know, as I'm sure you know, many, many people who think that more money, more X, more Y will make them happier, content or at peace. And they never reach that moving goalpost. And you and I also, I'm sure have come across, it's more common in Silicon Valley than, than Ottawa perhaps, but people who have tens of millions, hundreds of millions of dollars and are absolutely miserable.

• 1:37:33Speaker 03

  Right.

• 1:37:33Tim Ferriss?

  Uh, and is the feeling, feeling very uncomfortable with comfort, a symptom of lack of contentment? Or is it something else? If that, if, if that makes sense. In my time with you, you don't, you don't strike me as like you are not one of those miserable, miserable people. I've seen you with your family. I've seen you with your friends. Like you surround yourself with good people. Like I wouldn't be like, no, no, Toby's an unhappy guy and he's not going to be happy because he's just chasing this ever growing number, which is definitely not what you're chasing. And I can say that for sure. But is there an aspect of it that makes it hard for you to appreciate where you are currently? Or is it different?

• 1:38:16Speaker 03

  I think there is. Um, I, I, you're right. I mean, I, um,

• 1:38:22Speaker 03

  I, I have an incredible, like I'm the most fortunate purpose person on the planet. I sometimes think, right? Like I have an incredible family of three, uh, three boys, um, uh, wonderful marriage. I'm on a, I'm on one of those journeys at an incredible scale surrounded by friends. So, I have kind of a lot of things going, going on there, going for me. But I mean, look, I certainly have my demons too, right? Like, I do, like, I'm pretty serious that I'm going for minimal distance of the person I'm meeting at the end of a life to the person I become.

• 1:39:03Speaker 03

  I set very high requirements to me, partly because I know that I was the bottleneck of Shopify for a couple of years, around that sort of 2008, 2009 time period. It was just, I was holding this back and a lot of my, you know, family, friends or so are very dependent on this thing working out for all these reasons. And so I just, I just really don't want to get in this situation again. I need to, I need to challenge myself intrinsically to be ahead, like to understand what comes next, to, you know, for better, for worse.

• 1:39:44Speaker 03

  If you're running a company and you're sort of a product type CEO, you have to have a pretty good crystal ball about the future and where things are going. And it doesn't need to be always right, but it certainly should be more right than it isn't. Because you're taking, building software takes a while and if you're building against it now, it's going to be old in two years when it's done, right? And so you need to build against the state of the world in 2021, 22 and so on. So like, I'm chasing, like, becoming the best version of myself. And that has, a lot of good comes from that, but it's, it can also be stressful.

• 1:40:21Tim Ferriss?

  What, what do you think caused you to be the bottleneck? Could you define what that means to have been the bottleneck and why do you think that happened, right? Was it because you didn't know how to hire, you weren't willing to hire because you, for whatever reason, weren't expanding your skill set fast enough? Like? What did it mean to be the bottleneck? And looking backwards, how do you do the forensic analysis?

• 1:40:44Speaker 03

  I just did not make decisions that I had to quick enough. Like there was this whole thing about should I take like is Shopify a lifestyle business or a growth company? It's I struggled with this so much. It seems silly now because obviously we can all look at the result of it becoming a growth company at some point, but it was really unclear to me. And so I very I ran it cash based, like looking at bank accounts and making decisions based on, hey, I only I need this amount of money in the bank before I can put 5,000 thousand Google AdWords in front. And I just made a lot of decisions way too slow because I just didn't feel comfortable understanding the implications of them.

• 1:41:28Speaker 03

  And I didn't know I was doing this and I'm really unhappy with it, but I did and I'm really unhappy with it. I think I intentionally slew, well, unintentionally slowed down the growth of a company for a period of time so that I could stay on top of it.

• 1:41:47Speaker 03

  And once I only realized this after I finally made the call to just say, okay, let's get some venture capital. And once we had extra money and could spend it on all these like marketing campaigns, which we never did, it's like every single one we tried worked and the company just took off in a degree that is almost comical, like we see is still talking about those times as something that I've never seen before. Like I got I got my Series B, I think six or seven months after the Series A and they just gave it, they wired the money before we even started talking about it. It's like you need more money, like you didn't raise enough money, right? Because the numbers were so good.

• 1:42:27Speaker 03

  And so it's it's I just held it back and I don't want to do this again.

• 1:42:35Tim Ferriss?

  So why, for people listening, they're gonna be like, wait a second, Ferris, don't gloss over that. So everything worked. Why did everything work? Was it because you were bootstrapped? And I don't, you know, I'm not trying to answer the question for you, but was it because you were bootstrapped and therefore all of the focus was on the product for an extended period of time? Was it because of something else? Was it because you had a lot of interaction with your customers and therefore knew how to position things that when you turned them into expensive or more expensive campaigns, you had already honed the material? What were the, why did things work?

• 1:43:13Speaker 03

  Yeah, a little bit of all of us things like Shopify, then it came out 2006 was a brilliant solution to the problem of I need to start an online snowboarding store. That's it. Unless you happen to also want to make a snowboarding store, it was no good. And but I was the customer support on top of everything else. And, you know, here's the kind of interaction that happened all the time. It's like someone would send me an email saying, I cannot imagine like you're calling yourself an ecosystem and you don't even have this feature. And, you know, I'm on the other side of this email. I'm like starting to try to write an essay about why they're wrong. And it's clearly not coming together. So which then means

• 1:43:56Speaker 03

  I spent the entire night, I implement the feature. I deploy in the morning and I reply with an email saying, actually, what are you talking about? It's right here. So, you know, that on top of also having been a merchant and really understand like I was, I'm like, I was and I still am in absolute love with this particular problem. In the same degree, McPhee, sorry, McLean was in love with shipping, like shipping things. I'm in love with I, for this type of business, this sort of retail product based business, I just want to give people a chance to build, like to reach for independence and start something that's

• 1:44:39Speaker 03

  meaningful and become, turns them into an entrepreneur because I remember what it felt like when I did it. And so they spend years. Just chipping away at this problem, making it better and better, making Shopify better. It really came together around 2008, 2009. And then the financial crisis kind of just happened and we thought we were dead. But suddenly, at this point, it was actually quite good at this point. And it was also really cheap compared to everything else. So people started.

• 1:45:09Tim Ferriss?

  The service itself.

• 1:45:10Speaker 03

  Shopify was. Twenty nine dollars, right? It's not like we had people converting from like nine hundred thousand dollars a year bill to a fifty nine dollar plan a month, right? Like a month plan. So which of course tells you exactly how good I was at business at this time. But like, but for us, this was a point of pride, right? We love this. And so we, but we invested everything into the product. Like there was a twenty years in our mind roadmap, which we couldn't get to because we were this tiny team. And so, so again, in this timeframe, the software was really good.

• 1:45:51Speaker 03

  But then the people who used it loved it, but it was hard to get the word out. And so, but to test anything, I always had to like, every time I had five thousand dollars additional reoccurring a month, I had to make a decision to, am I going to hire this one person? Which is going to be really good for a product? Or am I going to spend this as a test for, in some kind of marketing capacity? And so what I ended up doing finally, and that was the right thing to do, is I got the top five ideas for marketing ideas. I saved up the twenty five thousand dollars so I could, you know, divvy that out amongst those ideas. And said, okay, let's try all of them. And like, because if one of them really accelerates our growth, then we are actually a growth company

• 1:46:36Speaker 03

  and we should get venture capital.

• 1:46:38Tim Ferriss?

  And we should know sooner rather than later.

• 1:46:39Speaker 03

  And we should have done sooner, right?

• 1:46:41Tim Ferriss?

  No, no, I'm saying you do all five at once as opposed sequentially, because then you get the feedback.

• 1:46:45Speaker 03

  Exactly, yeah, exactly. Because otherwise we don't know, maybe suddenly, I mean, it's, it's, it's a reality change too much. This wasn't still not very scientific, but it's more, it was better to do it at the same time. Because there are different ideas, like radio and adverts in this way and other campaigns in this way. And all five worked.

• 1:47:07Speaker 03

  It was stunning, honestly. They all worked and every single one clocked in better than what we expected a highly successful campaign should return. At which point I took this as an Excel spreadsheet to the venture capitalist and said, here's a formula, I need to fund this formula, right? And then this changed the conversation quite a bit.

• 1:47:32Tim Ferriss?

  They're like, Toby, I remember when you came here on a bike.

• 1:47:37Speaker 03

  Exactly, exactly.

• 1:47:40Tim Ferriss?

  Oh, my God.

• 1:47:41Speaker 03

  So it's come to a bike when I come to the formula.

• 1:47:43Tim Ferriss?

  The, as you said earlier, there's a lot of chance involved with a lot of this stuff, but you can, and I wish I could give credit to the writer who came up with this term and I'm blanking, you may know who this is, but they talk about a luck surface area and increasing your luck surface area so that chance has a higher likelihood of sticking. I know that's, there's a lot of, a lot of confusion in that sense, but the importance of that hands on those customer calls is sort of, I think, hard to overstate, right? And I know, I know some companies that require all of their executive hires to do a period of customer support.

• 1:48:29Speaker 03

  Same with us.

• 1:48:30Tim Ferriss?

  Oh, yeah. Same with you guys. Yeah, on the front lines.

• 1:48:32Speaker 03

  And I still do, I take customer calls. I do periodically. I work with customer support. And I have my own account there. I take some tickets and I take the phone and I go visit customers all the time. It's, you know, this is actually like distance to frontline becoming bigger has probably killed more companies than, from probably many other forces that people would immediately think about when talking about disruption.

• 1:49:00Tim Ferriss?

  Yeah, I love it. Toby, I'll ask just a few more questions and then we'll wrap. We have some dinner, maybe some wine or something else to have later. But you mentioned the crystal ball.

• 1:49:17Tim Ferriss?

  And the importance of looking into the future, particularly with the types of products you're developing and the technology that you work with. To go back to my notes. Here we go. John Phillips considers it his job to go in Lutka's office once in a while and get him to clear everything off his desk. As CEO, he feels he shouldn't have any actual work to do. We'll kind of gloss over that part. Quote, "He has guys to do that, and if he meddles in it, he'll cause a problem," which I like, this is pretty funny. But thinking, you have to be looking ahead. How does, this is just like, it would be a super fantasy of mine. Is it literally clearing stuff off your desk? What is, what does John or other people do to help get you out of the stuff you shouldn't have your hands in?

• 1:50:02Speaker 03

  Yeah, I, I mean, this has been such a journey, right? Like, I mean, I, I want to say I like the really high level strategic things, and I like the absolute tiny minute details.

• 1:50:15Tim Ferriss?

  Then you are also in the customer tickets.

• 1:50:17Speaker 03

  Right.

• 1:50:19Speaker 03

  The thing that I optimize away is everything between those two.

• 1:50:22Tim Ferriss?

  Oh, right.

• 1:50:23Speaker 03

  And so that helps a lot because, you know, again, these tickets matter, right?

• 1:50:30Speaker 03

  I think John has been, like, he has been such a massive help. He's the same person I mentioned earlier who came to me and said, "You'll never, Toby, you'll never find someone who's gonna care as much about Shopify as you do," which encouraged me to take the CEO role. So he was there at many important parts of Shopify journey, and I was full of good advice. And so he helped me sort of build out this practice over time to just hire good, great people for everything in the middle and allow me to think about the sort of long-term, big-picture kind of things. And, but I really, really, really do like going and putting my chair in some part with engineers working on some

• 1:51:14Speaker 03

  important performance details and so on. But that teaches me something about the company, and it also, it just, it allows me to access this. The latent pieces of mastery that I once built, which is actually, you know, you were talking about happiness and contentment, like tapping into some kind of mastery, you just can't. You can't spend all your time just working on things which are going to finish two, three years from now. It just doesn't, like the feedback loop is too long. It doesn't nourish you in the way that, like just doing something that's fun is to do now. So that's a really important component. But last year on this crystal ball, I mean,

• 1:51:56Speaker 03

  here's the way I think about it. I find that, like, so first of all, the future is not predictable. Like, a future is a random walk and depends on macroeconomic events and climate change and a million other things. So you can't actually know the future. But there are two things you can do. One is really important, which is just draw the trend lines forward, sort of like a minor version of what Ray Kurzweil would do, right? Just like in 2009, we knew that almost all traffic to Shopify would be coming from mobile phones by just looking at data and connecting two points and drawing it forward. But it was kind of predictable. Computers getting

• 1:52:40Speaker 03

  faster, you know, AR classes getting, being around and all these kind of things. Like, we should add those into our calendar to say, by then, they probably are very important and we should be aware of them. So that's one component. The other, much more interesting component, is you need to be a credible witness to reality and you have to have a model of what, this is currently January 2019, almost no one in the world knows what January 2019 actually looks like. Because of exactly what William Gibson quote you just talked about, the future is already there, it's just not evenly distributed yet. There it used to be that you could go to Silicon Valley and what you would see around

• 1:53:22Speaker 03

  you observing the things around you would be a pretty like potentially ninety five percent accurate rendition of the most up to date current version of the particular time you were in. So if you were an entrepreneur in Silicon Valley and you looked around you and and and you just said, okay, I'm I'm seeing what Uber did with making cars just appear by pushing a button on my magical piece of glass in my pocket. I'm gonna do I'm gonna try to disrupt the laundry industry. I'm gonna do it in that way, right? You just by osmosis kind of aware of what's possible. Now it's much harder. China is a much bigger

• 1:54:04Speaker 03

  component, for instance, like a lot of innovations coming from China. And and a lot of people have not realized that China is completely flipped on its head in terms of it's not just copying ideas from the West, it's actually delivering ideas like these fully automated supermarkets that people are talking about and coming to various cities are all over China.

• 1:54:25Tim Ferriss?

  Yeah, the way they use facial recognition to gamify citizen behavior in certain cities and WeChat, some of the features built into it's.

• 1:54:33Speaker 03

  Yeah, but yeah, I don't wanna I wanna steer away from sort of a moral and political side of China, but like I I think just looking at it through just what is life like in China? It's appreciably more futuristic than it is anywhere else by just they are in a post credit card world for WeChat Pay and all these kind of things. They they have it unlocks completely new business models for them. And so it's it's worth our understanding. But there's other things like who actually in the business world understands the video game industry? It's the biggest industry no one cares about, right? It's like so.

• 1:55:07Tim Ferriss?

  Yeah, I remember one time, no, I don't want to interrupt, but I will since I've apparently had too much caffeine, which is I remember one point, I know nothing about very little about video games, but I remember I was looking at because you see it all the time. If you go to say Rotten Tomatoes, you see the the box office earnings of the biggest movies in the world, at least domestically. And then I saw some of the the numbers for video game releases and it just it was a multiple of the entire total of the list.

• 1:55:35Speaker 03

  Yeah, yeah, the video game industry is a good deal larger than television, music and Hollywood combined.

• 1:55:44Tim Ferriss?

  It's incredible.

• 1:55:45Speaker 03

  Right. But it's also one of the most competitive environments ever. Like, it's a, it's, it essentially is a massive industry on the Hollywood model that a hit is everything that everyone aims at. One hit like clears the money from the industry. And so what these guys have found out in the video game industry about just game psyche is fascinating and hugely futuristic compared to what these sort of business people figured out. And so, so what I'm getting at is you do the trend line thing, and I think that's table stakes, and people just need to do a good job of doing that. But that's also not that hard.

• 1:56:22Speaker 03

  And then you have to look around the planet and just say, where is competitive fields? What tools have they figured, have the winners figured out in them? How can I import those back into the rest of the world? And I think through the intersection of those two disciplines, you can actually get a crystal ball and make assumptions on the future that start becoming reasonably precise so that they are better than not having them as guiding posts for making product decisions and so on.

• 1:56:50Tim Ferriss?

  Toby, the Oracle of Ottawa.

• 1:56:55Speaker 03

  That sounds so wrong in a way.

• 1:56:57Tim Ferriss?

  You shouldn't have just said that because now I'm gonna make it my job

• 1:57:03Tim Ferriss?

  to make that your next headline.

• 1:57:08Tim Ferriss?

  So let's wrap up with a couple of questions that I like to ask and listeners seem to enjoy.

• 1:57:16Tim Ferriss?

  I'll just go for some of the hard ones.

• 1:57:19Tim Ferriss?

  If you had a billboard, metaphorically speaking, to get a message or quote, a question, a word, he's lifted his glasses and scratching his eyes as I'm asking this. So that's, it's, it's a sign of-

• 1:57:29Speaker 03

  I know you asked this question, why was I not?

• 1:57:32Tim Ferriss?

  This is, that's a sign of approval.

• 1:57:35Tim Ferriss?

  What might you put on it? Can't be an advertisement.

• 1:57:38Speaker 03

  I mean, I'm gonna stay on topic. Entrepreneurship is precious and needs to be celebrated. That's what I would put on the billboard.

• 1:57:47Tim Ferriss?

  On the billboard. Besides the books that you've mentioned, are there any other books that you would put? That is, one that comes to mind is most frequently gifted or recommended. Doesn't have to be one book, could be whatever comes to mind.

• 1:58:02Speaker 03

  I mean, the most frequently gifted book is The Elements of Style, because I just, I like good writing.

• 1:58:09Tim Ferriss?

  That was not a passive aggressive thing to employees?

• 1:58:12Speaker 03

  Like, people hate getting that book, but like, a lot of, I think I might have fifty copies in my office, so like, it happens frequently.

• 1:58:20Tim Ferriss?

  John, by the way, great use on the semicolon, however, here's a gift.

• 1:58:26Speaker 03

  Yeah, it's more like, hey, I like the content of the memo, but like, I don't think you've written a non-passive sentence in a year. So like, I think we need to talk. So.

• 1:58:39Tim Ferriss?

  Not to like stereotype, but that's like the most German thing I've ever heard. We have to talk about your passive voice.

• 1:58:46Speaker 03

  Yeah, exactly. No, I mean, a book I love giving to people at the exact, like, I try to, of course, aim at the right moment is A Guide to Good Life is one of the best books I've ever read.

• 1:58:59Tim Ferriss?

  That's the introduction to Stoicism, William Irving?

• 1:59:03Speaker 03

  Yeah, exactly.

• 1:59:04Tim Ferriss?

  Yeah.

• 1:59:05Speaker 03

  I think that's the best gateway to rock into this world.

• 1:59:08Tim Ferriss?

  It is a great book.

• 1:59:10Speaker 03

  I read, absolutely, have you, did you read The Courage to be Disliked?

• 1:59:17Tim Ferriss?

  No, but I love the title.

• 1:59:18Speaker 03

  It is a, probably the best book I've heard in the last couple of years.

• 1:59:21Tim Ferriss?

  Wow.

• 1:59:22Speaker 03

  It's an introduction to Adlerian psychology, which is like, was sort of anti-Freud. They were sort of the two factions in the Vienna.

• 1:59:31Tim Ferriss?

  What was the name?

• 1:59:33Speaker 03

  It's called The Courage to be Disliked.

• 1:59:35Tim Ferriss?

  But the psychologist?

• 1:59:38Speaker 03

  I think Alfred Adler.

• 1:59:40Tim Ferriss?

  Okay.

• 1:59:41Speaker 03

  And absolutely fantastic. I mean, clearly a student of Stoicism, but I think he took it further. His concept of the separation of tasks is probably, maybe that would be another thing I would put on a billboard. Like, but it's hard to put on a, I think, I think it requires a little bit of context and explanation.

• 2:00:00Tim Ferriss?

  So what is the separation of tasks?

• 2:00:03Speaker 03

  It's just the basic idea of it's not your task to be liked, it's your task to be likable and someone else's task to like you or not. It's up to them, right? It's the biggest wedge between your psychology and someone else's that could ever be driven into it. And, and I think potentially a more tangible way of getting people into this mindset. And I think the Stoics who came at it through a very sort of high mindedness, right? Like they, it all makes sense, but it doesn't like, I think what Adler does really well is

• 2:00:36Speaker 03

  he developed tangible tools for, to facilitate a lot of this kind of outcomes that the Stoics, the sort of reasoning about. So fascinating book.

• 2:00:46Tim Ferriss?

  Courage to be disliked. That is, that is one of the better titles I've heard in a very, very long time.

• 2:00:51Speaker 03

  Agreed.

• 2:00:52Tim Ferriss?

  Do you have any parting requests, asks for the audience's last comments? That for now you would like to, like to make, anything you'd like to ask them to do, suggest that they might check out? Or any, anything at all that you'd like to say?

• 2:01:12Speaker 03

  Yeah, it's a big, broad question. I mean, like, again, like, we didn't really get into this too much. I sort of alluded to it, that probably enough. So like, I'm a huge fan of people just going for it, reaching for independence, being like, building businesses. I think it's, it's worthwhile for especially your listenership to sort of understand that there's no force in the law of the universe that makes entrepreneurship stick around. It's actually happens because governments and like various people made very deliberate choices to.

• 2:01:48Speaker 03

  Facilitated, reducing friction massively increases the participation in entrepreneurship. This is, this is not a plug of Shopify. Shopify is a player in the space. But actually, we need more companies to figure out ways to reduce the friction of entrepreneurship across the entire spectrum of how people engage in entrepreneurship. Because I think if we don't, this is gonna end up being a serious economical issue eventually. Because by the time people figure out like, why is employment going away? Well, small business employment is down. Oh, it's actually because there's small businesses are going down.

• 2:02:29Speaker 03

  There's potentially so many systemic effects in play that it's gonna be hard to undo a lot of the damage. And so I think it's an underappreciated area of entrepreneurship. It is entirely possible to build a company that's highly valuable by focusing on this. You don't have to go up market like the way everyone tells you to, specifically investor types. And Shopify proves out a way if you're looking for a kind of blueprint. And so I would love for more people to think about this.

• 2:03:00Tim Ferriss?

  When you're going into your Oracle toolkit with the crystal ball and surveying the global landscape, are there any particular countries or cities that you think are worth examining or modeling that do a good job? I don't know if Singapore would be an example.

• 2:03:17Speaker 03

  Yeah, I would say it's sort of Singapore, but it's also like Stockholm is another one. So which, what's going on in Berlin is really interesting, but also Shenzhen.

• 2:03:27Tim Ferriss?

  Shenzhen.

• 2:03:28Speaker 03

  It's it. I think visiting Shenzhen would be highly, highly.

• 2:03:33Tim Ferriss?

  And that's S H E N Z H E N, Shenzhen?

• 2:03:36Speaker 03

  S H E, yeah, I think so.

• 2:03:38Tim Ferriss?

  Shenzhen.

• 2:03:39Speaker 03

  This is exactly the kind of thing I have trouble with dyslexia, but.

• 2:03:44Tim Ferriss?

  Chinese is pretty hard for everyone who's not Chinese.

• 2:03:48Speaker 03

  But it's, you know, just because you go in the like the world's biggest electronic markets and you realize, hey, if I wake up early enough and make my goal to, I'm going to build my own cellphone, I can be done by the end of the day by just getting components in this place, right? And these buildings just don't exist anywhere else in the world. And that kind of everything is possible attitude is also shared by everyone there. And it's just, it's a, it's a, it's a, it's a really fascinating place. It's really interesting. So I think that's a, that's a place which you figured it out.

• 2:04:20Tim Ferriss?

  Yeah, that's, I mean, that has sort of a silver lining on what could be a very large systemic problem is that there are exemplars out there. I mean, there are cases to study. Toby, this is so fun. I'm really glad that we ended up having the opportunity to cross paths yet again and sit down. Of course, people can find out more about Shopify at Shopify.com. On Twitter, they can say hello to you at Toby, T O B I. And then Twitter, Instagram, LinkedIn, of course Shopify is on all these platforms and I'll link to everything in the show notes. I also have a Reddit link here and maybe you can explain what that is. There's a shake, shake of the head.

• 2:05:04Speaker 03

  Shake of head, no Reddit.

• 2:05:06Tim Ferriss?

  Yes, you, if you.

• 2:05:07Speaker 03

  I don't know how that made it, man. I thought it was anonymous on Reddit. This is no good.

• 2:05:11Tim Ferriss?

  Okay.

• 2:05:12Speaker 03

  So. New account.

• 2:05:13Tim Ferriss?

  That, that is, is, is not to be mentioned. The name that shall not be spoken. So, and I'll link to everything we discussed, the books and so on, the principles, philosopher psychologists in the show notes at tim.blog/podcast. As per usual, you can just search Shopify or Toby, T O B I, and everything will pop right up. Toby, thank you so much.

• 2:05:39Speaker 03

  This was fun.

• 2:05:40Tim Ferriss?

  Yeah, really good time. I've, I've always enjoyed spending time with you. You've remained, you've, you've, you started off very humble and understated. You remain very humble and understated, which I think is, is a real testament to, to you. And I think it is true, the companies tend to develop a cultural around the personality and attributes of their leaders. And you've just, you've assembled a fantastic team and built a wonderful company that's doing a lot of good.

• 2:06:11Speaker 03

  Thank you so much, Tim. And again, kudos to you two. Well, actually, thank you to you two. You were a big inspiration along the way. You're a massive help. Thanks for making yourself available when we needed you. And it was incredibly gratifying to spend, you know, that really fun day at the New York Stock Exchange, ringing that bell, being there together. So it's, it's, it's again, it's all about being on a journey surrounded by friends. So thank you so much for being a friend to the company.

• 2:06:40Tim Ferriss?

  Oh, my, my pleasure and what an honor to, to have been in the right place at the right time. Railscom. Renew.

• 2:06:50Tim Ferriss?

  And it is, it is, it is really important to have companions on the path. So many adventures ahead. And to everybody listening, thank you for tuning in and try to figure out which box you're in and check out some of the resources in the show notes. Thanks for listening.

• 2:07:10Tim Ferriss?

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

• 2:07:51Tim Ferriss?

  And it's very short. It's just a little tiny bite of goodness before you head off for the weekend. So if you want to receive that, check it out, just go to fourhourworkweek.com. That's fourhourworkweek.com all spelled out. And just drop in your email and you will get the very next one. And if you sign up, I hope you enjoy it. This episode is brought to you by LegalZoom, which more than 2 million Americans have used to help start their businesses. Past guests even, such as WordPress lead developer, CEO of Automattic, Matt Mullenweg, now valued at more than $1 billion, have used LegalZoom to help with their business needs, specifically in his case, to form his company. But LegalZoom isn't just for launching your business.

• 2:08:33Tim Ferriss?

  Their services include everything from helping you to manage changing tax laws, reviewing contracts, creating NDAs, non-disclosure agreements, important stuff, handling lease agreements, and assisting with really any other legal challenge, hurdle, inconvenience that typically takes time and effort away from running your business. The best part is that you won't get charged by the hour, because LegalZoom isn't a law firm, so they won't be running the clock up and spinning circles just to raise your bill. Instead, they just ask you to pay one low upfront price for whatever it is that you're looking to get, à la carte style. So visit LegalZoom.com and check out their business section for all of their services. And if you want special savings,

• 2:09:16Tim Ferriss?

  that's the terminology in the copy that they suggest. I don't know what the special savings is, folks, but it's titillating. If you want special savings, enter promo code TIM, T-I-M, at checkout. Capital T, lowercase i-M. Again, take a peek, LegalZoom.com and enter promo code TIM. This episode is brought to you by Peloton, which I've been using probably for about a year now. Peloton is a cutting-edge indoor cycling bike that brings live studio classes right into your home. You can also do on-demand, which is what I do, we'll come back to that. So you don't have to worry about fitting classes into a busy schedule or making it to a studio or gym with a hectic or unpredictable commute. I, for instance, have a Peloton bike right in my master bedroom at home,

• 2:10:00Tim Ferriss?

  and it's one of the first things I do many mornings. I wake up, I meditate for a bit, then I knock out a short 20-minute ride in my undies, hard to do that at the gym, take a shower, and I'm in higher gear for the rest of the day. It's really convenient and has become something that I look forward to. So you have a lot of options. For one, if you like, you can ride live with thousands of other riders across the country. Country on an interactive leaderboard to keep you motivated. There are also up to 14 new classes added every day with more than 8,000 classes on demand and you can pick based on length, 45 minutes, 20 minutes, whatever. Music, hip hop, rock and roll, or say low impact versus high intensity or interval. You can pick the class structure and style that works for you.

• 2:10:41Tim Ferriss?

  And in my case, I quite like Matt Wilpers and I tend to do on demand and listen to a lot of and watch many of the same classes over and over. But I'm kind of promiscuous and also enjoy classes from a lot of the other instructors. They have Peloton, an amazing roster of incredible instructors in New York City with a whole range of styles and personalities so you can find what you're in the mood for. You also get real time metrics that you can use to track your performance over time and that will help, I would say catalyze you to beat your personal best. Now that all sounds good, right? Gamification, yada, yada, yada. I didn't think that it would work for me or in any way incentivize me, but they really 100% hit the nail on the head.

• 2:11:21Tim Ferriss?

  I was very, very impressed with how motivating it was and it worked tremendously to keep me pushing, which quite honestly takes a fair amount. I can get quite lazy, particularly with anything that edges on endurance, which is kind of more than five reps of anything for me. So, check it out. Discover this cutting edge indoor cycling bike that brings a studio experience right to your home. Peloton is offering listeners of this podcast a limited time offer. Go to onepeloton.com, that's O-N-E Peloton, P-E-L-O-T-O-N dot com and enter the code TIM all caps at checkout and get $100 off of accessories with your Peloton bike purchase. So, get a great workout at home anytime you want. Check it out.

• 2:12:05Tim Ferriss?

  Go to onepeloton.com and use the code TIM to get started.