Shawn Ryan Show - #261 Tobi Lütke - CEO of Shopify: How Shopify Became a Cheat Code for Entrepreneurs

Episode Date: December 11, 2025

Tobi Lütke is a German born Canadian who built a multibillion-dollar company from a snowboard shop; champions economic freedom for regular people starting businesses; combines old-world craftsmanship with modern innovation. He is an entrepreneur, software developer, best known as the co-founder and CEO of Shopify, a leading e-commerce platform powering over 4 million merchants worldwide as of 2024, generating billions in annual revenue. Born in Germany, Lütke discovered his passion for coding at a young age with a Schneider CPC computer, rewriting game code by age 11. A self-taught programmer who dropped out of school after tenth grade to pursue a computer programming apprenticeship at Koblenzer Carl-Benz-School, he moved to Canada in the early 2000s. In 2004, as a snowboard enthusiast, Lütke co-founded Snowdevil, an online snowboard shop, but frustrations with existing e-commerce tools led him to build a custom platform using Ruby on Rails, which became Shopify in 2006 in Ottawa, Canada. Under his leadership, Shopify went public in 2015, reaching a market capitalization exceeding $100 billion at its peak. He is a core contributor to Ruby on Rails and creator of open-source libraries like Active Merchant. Lütke joined Coinbase’s board in 2022. Tobi is a competitive racing driver in the 2025 IMSA SportsCar Championship’s LMP2 class for Era Motorsport. He is married to Fiona McKean, a former Canadian diplomat, with three children. He co-founded the Thistledown Foundation, supporting environmental causes through initiatives like Shopify’s Sustainability Fund. Lütke advocates for ethical technology, small business empowerment, and innovative leadership, often speaking on platforms like Invest Like the Best about building sustainable tech ecosystems. Shawn Ryan Show Sponsors: Visit https://shopbeam.com/SRS and use code SRS to get our exclusive discount of up to 50% off. Go to https://ShawnLikesGold.com right now to get your free 2025 Gold & Silver Kit. Ready to upgrade your eyewear? Check them out at https://roka.com and use code SRS for 20% off sitewide. Upgrade your routine with Caldera Lab and see the difference for yourself. Go to https://CalderaLab.com/SRS and use SRS at checkout for 20% off your first order. Tobi Lütke Links: X - https://x.com/tobi IG - https://www.instagram.com/tobi Get started with Shopify - https://shopify.com/srs Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Hey, what's up, y'all? Kelly Clarkson with Wayfair. My favorite thing about the holidays? Dacking out my whole house. It's not a competition, but if it was, well, I'd win the season with Wayfair. Outdoor inflatable Santa? Got it on Wayfair. Trees, lights and ornaments? Wayfair.

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But, you know, I want to start this off. I feel like I owe you a thank you. I don't feel like I owe you a thank you. How so? Because what you've done with Shopify has just, it's it is what brought success to my business and so many others and so i'll just give you a story you know when i started this in around 2015 actually in december 2015 so almost exactly 10 years ago and you know this kind of started as uh is a is a tactical training company and i had just

gotten i just left cia contracting for the cia i didn't really know what i was going to do and I've always wanted to, you know, get into entrepreneurship. So I started this company and, but I had no money. And web developed, you know, to create a website back then was, I mean, it was, it was, for me, it was a lot of money. I mean, it was, if I remember right, it was about $20, $25,000 to get a website made. And I was like, man, I don't have $25,000. But I did it.

I did it. And I got a shitty website. from a developer who I needed to call and have meetings with about every day, every time I wanted a new product out there. And I was just selling courses. And, you know, of course, every time I wanted to add another product, that was several thousand more dollars. And then I think it was TV.

I was watching TV and I saw a Shopify ad pop up. And, you know, it was talking about the do it yourself stuff. And I was like, man, maybe I should try this. And so I did, I got the free trial, I tried it, and I was like, holy shit, I just built an entire website in like four hours. That's amazing. And, you know, and that was 10 years ago, and we're still on the platform to this day. So if I have a story like that, and we started, so I started selling my courses on there, and then the really, the big win for me on Shopify was dummy bears. So.

which we still sell today. That's a bag for you made here in the USA, sold on Shopify. Love it. But it's such a good pride. But it just, I mean, it's just, it like unleashed a cheat code to entrepreneurship by being able to sell our stuff

because web developers would hold us hostage and so thank you for doing that. I mean, that's so meaningful to me To me, because, like, again, this is my favorite story, right? Because it's like, I think entrepreneurship is incredible and incredibly important. Like, it's so important for society that people can, you know, reach for independence, that people can, like, instead of complaining about something not existing, they can actually do something about it, they can build something and there's a wonderful market, you participate in it. And if the market deems it to be of value, then, you know, it funnels coin back to you so you can do more of this thing and it all kind of virtuously kind of grows in a virtual

cycle. And it's just so honest. It's like it's such a form of self-expression. It's such a way to not just like gain, but also give back. And it's perfectly positive sum. So from a just fully philosophical perspective, it's one of the greatest journeys people can go on most people. And it does require a good deal of courage to put yourself out there.

But I've started early my teenage years with small businesses and just selling products and these kind of things. And I've discovered this for myself, and then later, I'm sure we're going to get into some of these things with my snowboard shop and so on. And I love that after discovering this sort of gift and like trying to figure out how to, like, sort of in my own mind, how to build these businesses, that now we get to like spend all our time, like really day and night, creating a product that we can share, which itself causes us. people to share their products right like this is a wonderful thing it says millions of businesses out there that provide employment that create new products and so it's but it's the important thing there from my perspective is I thank you for for building something because you know like as you know

especially for the builders like if there's not nothing in the world more gratifying than someone using the product or being delighted by the product. So I think that's honestly the best thing about the world of retail commerce is like it's accessible, it's available, and it's really, really, really, there's a lot of camaraderie, there's a lot of, because everyone has so much in common with each other, everyone's engaged in it, and her respects each other for doing this. So, yes. It's, I mean, you have just, I mean, it's, I mean, I can't just, I just can't stress

it enough. I mean, you know, it's not like I just took that 25,000, you know, and spent that on bullshit. Like, as an entrepreneur, it could have been. It's a huge lift. You could have called it at this moment, and then you would have been $25,000, $20,000. But I mean, I see, I just have saved so much of web development. And, you know, in taking what I saved and putting that into, you know, product or other areas of the business.

Because, I mean, if I remember that I'm off on these numbers, but let's say 20,000 to build a website, then Shopify, I find Shopify, and it's like $20 a month. And it's like, holy shit. So I was able to take all those, all that capital and put it towards something else and build something real. And so I'm just one of probably millions and millions of people who use Shopify, who found success in entrepreneurship because of what you built. And that is amazing. That is amazing. I mean, I read something the other day that said Shopify is getting close to surpassing Amazon on web sales. And, you know, that is, wow.

I don't know exactly what number that is and what angle this is. but like, and we are actually working very closely with Amazon, but like, yes, it's big, you know. Like, again, it's millions of small businesses. And the thing that happens, when if you put a lot of small things together, you get a very, very large thing. Many, many, many little lights make a sun.

And it's, it's about 10, 15% of all of commerce in the United States online now when you put it all together. And, yeah, I mean, trillions of, like, over trillion dollars, almost a trillion and a half, has been transacted through the platform since its inception. And it's, yeah, I mean, those numbers are insane to me, right? Like, it's because, you know, I've been around for, like, I started a company 21 years ago, so, in 2004. And so I remember, like, when it was tiny, right?

Like, I remember when we had a party, um, uh, uh, then I think it was a hundred million dollars was transacted for a platform which sounded like this and it is this incredibly high number I mean I think that's like a couple seconds now it's just like incredible so you know I'm I'm really fortunate that you know this project worked so well and again that you know I want there to be just more people experience and saying basically what I did when I started my business. Like this moment of, let me ask you, like,

do you remember still when you got your first sale? I do. I remember it because I was putting courses up online. I couldn't get anybody to buy a damn course. And I had a guy that told me, hey, mark everything sold out and then and then remarketed out there and uh and i did and the very next time i sold the course out like that but uh love it yeah yeah do you do remember um uh you remember what course it was and like did you remember like what did you think then that happened like

i think i mean it was uh i mean it was it was it was just it was incredibly meaningful it was the first It was the first real transaction. It wasn't somebody doing a favor like, oh, you know, you just started a business. Let me buy the product. It was almost like pity. You know what I mean? I don't know if you've ever had that happen where it's like, you tell a friend, you start a business like, oh, I'll buy a couple bags of those got me bears.

It was somebody that, it was a big deal because it was somebody that never had met me, you know what I believed in what I was selling and bought it. Right. You know, someone who, like, people do not like to part with their money. Like, to purchase something, it means, like, the thing that you clearly value very highly, you're giving up because you think the thing that you're getting there is of more value to you. And that's an incredible, like, there's no virtue signaling at all at play. This is just a transaction, which is the most honest vote that anyone could make for this product existing.

Every single time anyone purchases from anyone else, it is a vote. It's actually, you know, we talk about in politics you get to vote, I mean, every two years, every four years. We vote every day for the future. We vote because, again, every single time someone purchases something, people purchase the gummy beers. you vote not just for that product, but also for everything behind the product, for every part of how it was created for the supply chain behind it, for the people who were employed at the places that manufacture it, for the postal service, and so on.

So tomorrow looks infinitesimally much different because of today, because of the transaction. People have seen this sort of at the local level. If people vote with their dollars for the local boutiques, they thrive if they don't and purchase everything from the department store or supermarket, then they will go away over time. And so it's actually a really, really, really important thing. I remember everything about the day when I had my first sale. Again, I built my snowboard business and it was a gentleman from Pennsylvania who I've never met and I've never talked to and who purchased a snowboard for me and you know it's a

funny it's a specific or somewhat unique perspective there because of course when the person purchased from Snowdevil, Snowboard store, he was interacting with software that I wrote. So that software you write will never do anything that you didn't tell it to do, right, outside unless they have bugs that you're trying to avoid. And so after the purchase, the software sends an email, like to me that there is a purchase that I now have to deal with. At some point, a couple months earlier, I wrote that email, like hoping that at some point

the software would have to send it. You don't know, I didn't, could have been a failure. I didn't find any software in a market in 2004. There was nothing for starting Snow Devil that was at all possible to use or that I could afford, so I built the software myself. And I, so I sit at a coffee shop, you know, staring an email inbox, you know, staring an email inbox, looking at an email that at some point, a couple months before, I wrote as a template,

but this time, like, with all the variables filled in, like, gentlemen in Pennsylvania buying this item. And I just had this profound moment. It's like, holy shit, I just went from being a builder to being an entrepreneur today, right, this moment. Right, like, it's like, you know, my children think of me as an entrepreneur now, and maybe my grandchildren, will one day because of that day, right?

Like, it's like, that's a long distance traveled due to staring at one email. And so, again, it's just been this, I think sort of in my mind, I just couldn't get that moment out of my mind. It was just like, this is, I wanted to share it, so I tried to tell people, but they're like, oh, that's good for you. It's like, people are like, you can sort of describe it, but you can't take people back to that moment.

So, so, and, you know, when I, you know, Snowdivel became, grew a bit, and I got these messages from people saying, would you license your software and then, you know, made the decision to spend another year and a half and then 2006 launched Shopify, which really is like the software I wish I would have found back when I was. You know, try to make it simpler for people to start. And yeah, to this day, like, from this moment, like, every time we make it slightly simpler again for more people to start, more people succeed, and it's been super gratifying. If I was able to figure it out, I think damn near anybody can fucking figure it out.

No, no, no. It's like we can still make it so much better. There's a lot to learn. It's, again, tons of respect for every entrepreneur. out where we'll put some stuff so it's tough let me uh let me give you an introduction here real quick toby ludkey entrepreneur co-founder and ceo of shopify shopify is an e-commerce ecosystem used by over four million merchants generating billions in annual revenue you're a snowboarder race car driver and philanthropist board member at coin base since 2022 in 2003 you moved to

Canada from Germany where you became a citizen. You regained your German citizenship in 2022, holding dual nationality. You live in Ottawa with your wife, Fiona, and your three children. And once again, like, thank you for what you've built. We've been using that for 10 years. And, you know, I want to do a, you know, a journey on how you build Shopify. And then we have just a whole bunch of topics to cover that all have to do with an entrepreneurship. But, But before we get two in the weeds on your story of a Patreon account, built a subscription network, we've turned it into quite to the community. And so one of the things that we do is we offer them the opportunity to ask every guest a question. This is from Eric Alger.

What's the single most overrated thing in tech entrepreneurship today? Networking events. Networking events. That is not what I was expecting you to say, but I took it totally see where you're going with this. I just like, I try and I really, really try and I'll try to make a book, but it's just like I can't. I'm like maybe I'm the wrong person to try. I'm trying to like, like what's, this is sort of a flippant answer, well, what can I share that's actually actionable? I'll stay on the topic and maybe make a modification.

advice I think you know I think advice is overrated I think gut instinct is underrated I think we need like too many companies are building slightly different versions of something that someone else already sort of discovered or slightly different takes on things and do market research and AB test everything. And at least in my corner of a world in retail industry, you see more self-confident this thing needs to exist. And I think that would be nice if tech becomes a little bit more weird, a little bit more eccentric and a little bit more self-confident and leaning into uniqueness rather than

derivativesiveness more again. I think the AIH makes this so much more attractable for most, so I'd love more of that. Right on, right on. I love that answer. We're going to take a quick break real quick, and then we'll get into your life story.

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deal before it's gone. All right, Toby, we're back from the break. So we're getting into a little bit of your life story here and how Shopify came to be. So I know you came here from Germany. What brought, or came to, excuse me, came to Canada from Germany. Well, the best reason, wonderful Canadian woman. So, like, that's, I, my wonderful wife is Canadian.

And we were living in Germany and, like, decided, like, she has, I mean, we were really young. She then back to study do her master's degree in Ottawa, Canada, and I moved with her. Nice. You know, I grew up in Germany, like, being, I'm computer. guy, as is probably surprised to literally no one. I spent my teenage years more in dark rooms exploring what computers can do than in, you know, dark rooms at raves, as I probably should have. And given this was the 2000s in Germany or late 90s.

But it's funny, sometimes friends ask me, it's like, hey, how was, what was the techno scene like in the 90s in Germany? I'm like, yeah, I wish I knew. So, like the, so, you know, like I, being very much in computers, I knew of Silicon Valley, I never was there, but like, you know, Canada was certainly closer to that. And I figured, so I'm, you know, I just sort of make my way there over time and then learned everything about Canada and really, really fell in love with a place. So that's where I am. Nice. You've been there ever since. Ever since. And so you moved to, if I remember correctly, moved to Canada, marry your wife, and start a snowboarding shop. Yeah. So funny story. I did, again, I, well, I left school pretty early, I should say. Like, this is not super unusual in Germany. There you can, after 10th grade,

you can decide to do an apprenticeship instead of doing three more years in school. And I apprenticed as a computer programmer because I basically was just like, hey, like, this is what I need to do. It wasn't exactly a good student, but like I was good at learning things quickly when I needed them, and computers were much more interesting. So I apprenticed as a computer programmer under Meister by the name of Juergen was a wonderful character and taught me the taught me the ropes. And so coming to Canada, then none of this was officially acknowledged as education, and therefore there was no way to get a work permit properly. And so I was sort of on a visitor visa in Canada,

and then eventually as we get married and my wife could sponsor me as a family. You know, just like I, it's like, so all I say this is for 40, reason. Turns out if you don't have a work permit, you can't work. Pretty simple concept. I tried to get hired and then people pointed this out to me. And luckily, one of the lawyers, then I just ask a lawyer, friend, or what I should do, he said, well, I guess you can't work, but you know, you can start a company. You don't actually need to permit for that. You're not technically working for anyone because while you're starting a company, your official status is unemployed, right? Like, this is actually what's happening.

So I'm like, okay, cool. I mean, that makes sense. I always, like, sold products to my classmates in school. I, you know, just like, this is how I made money anyway. Like, I can start an internet business. I know computers really well. And so, again, this is when I decided, like, you know, I was also, turns out Canada's pretty cold. I noticed, it's like, it's like, In Canada, you can't run, at least in Ottawa, where we live a living, you can't run the strategy of, like, treat winter as something that just is temporary and you just wait inside until it's summer again, you know, like, it's too long, it's too cold. So you really need to get outside, and so we began snowboarding, it's fun. And so I spend a lot of time, you know, snowboarding, learning verse, learning, getting deep into gear and figuring out what's good and what's happening. So I just combined those two ideas at this point and just said, okay, I just know a lot about snowboards and I know a lot about technology.

If I put them together, I start an online store saying, snowboards, good, let's go. And then I tried a bunch of software. I'm not going to bore you all the details. This was all kind of, again, we are talking 2004. It is really a long time ago. Software was... We barely had broadband. We barely had like...

web browsers. Internet Explorer 6 will either tell people in the audience nothing, or will send a shiver of fear and dismay through them. It was like terrible stuff. Anyway, I'm a programmer, I just start programming, I built this online store just for myself, loved the experience of making all my own decisions. I'm the kind of person who probably can't truly work for other people anyway, so maybe not having a work permit wasn't all that bad.

So I just love this like independence that I was getting. Had you felt that independence before this point? Certainly my parents have, and probably my teachers too. So yes, I think so. I think there is a pretty large, probably larger than we generally admit percentage of people who are who should be not working for other people and should be doing their own thing and creating their own music and so on. It's probably, I think everyone can acclimatize to other situations,

but on balance, it's a fairly common streak, I think, and those people, this is partly why I love those consequences of Shopify is that more of these people can try, but I don't want to get ahead of the story. I, yeah, so I decided to, like, build the software, use really esoteric programming languages, which spoke to me and whatnot. And then I launched it in August 2004,

and we had, you know, made this for sale, which was this life-changing experience for me. And, you know, Snowdevil worked and we sold snowboards. They were all in my garage, my business partner's garage, actually. And, you know, we just took them to a post. It just like all kind of, it wasn't a big operation. But, you know, we made money and we found success. But then, like when people stopped buying snowboards because it got warmer,

at least most places. It just was kind of clear that the big discovery of the season wasn't the business itself, but like actually helping other people do the same thing. And that's why Shopify exists. Holy shit. So within like six months of you creating the online snowboard business, it turned into the beginning of Shopify? The decision happened within six months. It took me a year, like way longer.

than I thought. The initial version of Snowdevil took me two months to build, basically. And then turning it into something that other people could use was, it took a year and a half. Wow. Me and a friend who came over halfway through. Yeah. But the idea was almost immediate. It, not just immediate. It was so, it had power.

You know, you know, it's, it's... It's hard to talk about these things in terms of energy, but there is... You feel it. You feel it. I got one cooking right now that I can feel. I know it's going to... I know it's going to go. And you just know, right?

And it's like... It's like... It's an energy source that you could have. What's building? Building things is you're converting something. You're converting some form of energy. It's coming from somewhere. It's like, sometimes it's passion, but I think it's more like, I, I was angry, actually, at the, how shitty the software was that I found when I tried to do this thing.

I'm like, God damn it, I want to start a business here. I am, again, I spend my entire youth cultivating skill sets, rare and luckily useful skill sets. around computers. Most people didn't. Why the fuck is there not better software here for everyone else? Like why do I need, why is in 2004 the only people who can actually create new business on the internet, which is clearly one of the things that happened that is of the greatest possible economic equalizer.

or so we hoped of our times. Why do I need to be a programmer to then become a retailer? That doesn't make sense. That's a small set of people. And why is the software that I can find so unbelievably expensive or so incredibly bad, that that's not right? And to me, I can channel this sort of dissatisfaction with the status quo as this unending well of energy

that I can convert into building. And I think there's many other power sources that people tap. Creates an internal drive. But it got to come from somewhere. Like, room temperature does not lead itself to forging things. You can't build something at room temperature. There needs to be a stronger emotion.

There needs to be guilt, shame, anger, like something strong. And then ideally something that's... that doesn't flame out fast, ideally something that lasts. So therefore, like everything that exists, everything that's built is a passion project by people. It's people who pursued and created something, usually in the face of naysayers and people who wanted to detract from that. And so that was it for me.

It's a combination of pride in my craft. and I'm literally a crafts person, I apprenticed my craft as computer programmer, and dissatisfaction with what my priors have prepared before I needed it. And so I want to make sure that the people who come now to entrepreneurship, find tools that are as good as I can make them. They always can be better, but that's the fun puzzle of a company. it's like it's it's it's never perfect but it hopefully is always better than it was before and so that's the thing that i just find to be the most fun things to dedicate my working life to we see it we see it all

the time here because i mean like i said because we use shopify but you know i mean i just want to um i just want to say like the the backstory you know to summarize it and to kudos to you i mean you're solve two problems with with I mean just the fact that you know Shopify was legitimately boring because you couldn't get a worker's visa and the and the only way to make a living was to start a business because it was illegal for you to work I mean that in itself is what a hell of a story you know what I mean and then we move into the it so you solve your own problem right there okay I'll start a business instead and then you of, you know, a world problem for entrepreneurs a year and a half later.

I mean, that's that is, that's wild. No, to be fair, a year and a half later, while Shopify launched, I'm going to say it was pretty good if what you wanted to do was happen to also start a snowboard store. Like it just took a lot of additional work to make it work for a snowboard store. like most other products. You know, if a product was very simple, you could do it. But like, it's funny. It was, you know, there's this old

sort of a riff on the JFK quote that people say in the startup ecosystem. We do with this not because it but because it is easy, but because we thought it would be easy. Nice. So there's a lot of ignorance that has also led to committing myself to this particular course of action, but it's also like wouldn't trade it for the world. I have something in the outline that says, building when nobody's watching and the importance of doing that. I mean, what is the importance of doing that?

to you. It's... I'm sorry, I didn't quite catch... So, building when no one's watching, years of... I see. ...of thankless work before any recognition. I just... So, I mean, again, I do believe in craft.

I do believe in honing craft. I'm sure you and I will find lots and lots of agreement there. It's like deliberate practice. And just like, I find, like, again, And it just matters what you do then it doesn't matter as well. And it's not just that you have to be on. It's also like the way you do anything is how you do everything. It's another way to put this.

I, you know, to me, like my core craft is computer programming. It's not what I spent really most or any of my day doing at work, but like it's like, it's the specialization by which I came into everything else that I then learned. And so it's like the trunk of the tree of my knowledge. It's like engineering principles and programming is the trunk, and any of my business skills is a branch, and then what people sort of observe on outside of the leaves, if you want to follow the metaphor.

I want to still grow my trunk. I want to understand and play with tools. I want to go and spend the Saturday evening just like, like sometimes just rebuilding something that I built in the past just to see how what I've learned and how if I can do it better now and have these kind of projects. This is especially useful if you are building something that's going to take a long period of time.

It's like there's no attention on it. Like it's like it doesn't matter. You need to be intrinsically motivated to want to move forward because there's no one really holding you accountable. There's like once your product is in market, things actually get easier. At this point, you have customers with, like, delightfully will tell you everything that's ever been wrong with your product every time you talk to them.

And it's like, which I love. And, you know, it's really, it motivates you, and motivates me too, like, I, especially, you know, early days is, again, Shopify is now out in the market. We're in 2006 customer support is support at Shopify, which also comes to me, right? Because where else would it go? And I will support, I will respond from support at Shopify.com, but it's still me. So people send these like essays about how can you call yourself an e-commerce software and not even have feature like this?

My initial response is like to write defending my product. And then I'm like, actually, very right. And then so next thing is, I don't spend the night to implement a good feature and then respond the next day saying, what do you mean? It's right here. So, you know, that's how you're right. you make products better. This is the loop, and that's just what you keep going. So how can you be intrinsically motivated to want to hone the craft? That I don't know. I think it's that internal

drive. I mean, you know, the way I took that, you know, what we're talking about right now is quit looking for a pat on the back, quit looking for an add-a-boy, quit looking for recognition, just build your business, and all of that, all that shit will come later if you find success. But right now, what matters is building. And, you know, I mean, we had a saying in the SEAL teams before that also relates to this. Where basically we had adapted the mindset that, you know, when you're not training, the enemy is. An entrepreneur, if you're not building, your competitor is. while you're out there fucking around at the bar, you know, doing a hob, not working,

your competitor is getting better and better and better and better. And that is a, that's a mindset that I took from the SEAL teams because, you know, if the enemy's training them, we're not, then we're dead. And I've moved that over to business to where if you're not building, if you're not innovating, your competitor is, and they're going to pass you up. That's right. And the question is how to even, like, is it possible to disconnect even from the need to have a competitor that might be training? I have mixed feelings on that.

Do you? I mean, I think a competitor can be, for me personally, when I built a podcast and I built a look and everything. And a lot of podcasts looked a lot different. I'm not fucking tooting my own horn here. But I looked at the market. I saw what everybody was doing. Everybody wanted to be Joe Rogan. That was it.

You had a purple curtain. Yeah, a bunch of shit on a desk that means something to you or it doesn't mean anything to you unless you're, you know what I mean? Like, Joe's got all this stuff there. Everybody just copied Joe. Everybody just copied Joe. And I took a look and I saw everything and I said, this is what we're doing is going to be totally different. and all of this stuff not that it's never been done before but it's never been done in a podcast setting and it's it's it's it's it's you yours it's something you build it's your aesthetic

and it's not um and all the centerpieces are things that come come from the visitors of your of your podcast it's like it's it's it's like you build something that's situated in the center of the they community that you built, which is a completely, like, it's a completely different, like, approach. It's not better or worse, it's just very, very different. And this is what I mean with, like, all the interesting things come from, like, doing differently. It's like exploring the different paths. And it's incredible how much people, like, so many people externalize so much of how they judge if something is good to running it through an internal focus group of how they think everyone else thinks and it's like how that sounds really

exhausting like that sounds hard also and i'm not sure it's going to be precise right like because we don't really know all the other people that well right like we sort of like maybe have a guess but But like, how about just doing things that you really, really want to exist, right? Like, and it seems like such a basic idea. But, like, I just find so many people that are just like, they think there's a game out there that they want to join, which is called the podcast game. And then they look at for the rules by looking at the podcast that are the most successful. And they think that if they apply, like, if they intuit and extracts, as many of the rules as laws and then adhere to all of them,

they might get the same results. You familiar with cargo cults? No. It's one of my favorite sort of World War to adjacent story. So Pacific campaign. Obviously, other than the I think B-22s, no, none of the planes had any rate.

planes had any range, right? So to fly into Japan, you really had nearly airfields very, very close to Japan. Some of the islands there had indigenous people on them. And so the American bases were built, landing strips were created. In some cases, this was the first time any of the indigenous people there had any kind of context with the outside. They were built. previous contact with the outside came from, you know, every once in a while a wooden crate, which was how old shipping was done there, like would wash up at shore with things in them, magical things, goods of society. The people who went, like, got these items, they call them cargo, of course, you know, just

like, that was a status symbol. And here the Americans, which of course all the people could observe in these airfields doing these things, and planes come, and what we bring, more and more cargo, which of course is like means was a very, very rich individuals and, I don't know if they thought about the people they observed as demigods, but they might as well. So now that World War II is over, and no one's going back to these islands for a while until people do. And what they find is that they're still running the airports. There's like the shamans are wearing like coconut shells like headphones in straw towers,

making sometimes noises that sound vaguely English. There's straw airplanes on the runway and people are doing this because they want the cargo to come back. And it just tells you something really, really important. I think about the human condition. We copy behaviors to try to create the same outcomes. And we do it all the time. So much of the business world, if you look at it, is just people cargo culting. I've noticed.

It's like... It's like putting flame stickers on the side of a car to make it go faster, really. It's kind of, it's not principled thinking. principled thinking. And so other people live in everyone else's mind, and I think disconnecting for me as much as possible is important. And I think when you talk with the grades in some categories like artists or so, they just need to paint. They have so much painting in them. They need to get it out, and they just don't care if there's a market for it. I got a question for you.

I mean, just, you know, as a business owner, because I agree with everything you're saying. Because I never, you know, I took a peek because I didn't want to do anything that anybody else was doing. I still do that everyone. I still do it every once in a while. But I never, I never watch. I never, I never, I also never want to look at something and then copy it. So I purposely stand back. You know, so it's kind of contradicting myself.

But I'll take a peek, you know, as I scroll and I'm like, oh, yeah, that looks good. That looks like shit, whatever. You know what I mean? But I'll never, I will never dive in and study what people are doing because I don't want to subject myself to wanting to copy what they're doing or manipulate what they're doing in my mind and do my mind. and did my own idea. I want everything to be 100% original. But at the same time, you know,

I would look, I think competitors can drive you. I saw a lot of people that I thought were competitors start to copy what I'm doing. My competitors, I mean, it's funny when you start business who you consider your competitors to be and then if you do find success looking at who your competitors are years down the road i mean it is it is it is fucking wild you know what i mean and now you know my competitors are the are the top people in the game who are actually friends but i guess what i'm saying is you know along my entrepreneur journey i mean i don't i feel like maybe I may have needed competitors is a driving factor because I'm a very I'm competitive you know what I mean I mean I've been competitive since a young age and I enjoy it a healthy competition and uh in that

competition drives me so I'm just I'm just curious I mean I can't imagine a world where you know and also looking at competitors I mean somebody that's a little bit ahead of you or maybe a lot ahead of you. I mean, it shows you what's possible. Like, it's a real living example of what's possible within your realm, which can, you know, that can be a driving, I fucking want that. You know, and that, and because this person's achieved it, it's achievable. And they're not that far from me, you know. Do you have any thoughts on any of that? I completely agree. The different, um, when you look at a competitor, it depends on what you do with information. Is it like envy or is it like, are you looking to copy or, again, like, cargo cult

with things? No. Like what you're describing is a rivalry and that's a totally different thing from competition. Galvanizing a rivalry is good for both sides that makes everyone better because I think I think this is an important thing. Like I don't think Shopify and Amazon have ever really been competitors. We have been rivals at times. And I think we inspire both like each other,

but we do it in a completely different way. And so I think that's a really, really, really healthy thing. I think what I don't like is when people skip the step of like having their own aesthetic, wanting to build their own picture and then use everything else as everything we're doing, everything else they're perceiving and seeing as additional inspirations to do a better job creating the unique thing that they want to do. And I think that's a, it's probably not a super like simple thing that I'm describing here

and maybe the difference isn't as important as I'm making it out to be. But somehow to me it is, it's like I really, really, I value rivalries with, and I find that obsession with competition is often, like, let's put it another way. Again, I'm a, I'm a motorsport enthusiast. I love motorsport racing. I grew up with Formula One. I get to know race cars myself. Were you at Formula One the other day? I was not there yesterday, no. Oh, man, I want to go so bad. Growing up in Germany, coming to Canada, suddenly no one gave a shit about Formula One, and it was a hard adjustment for me, and thank you Netflix, I suppose.

No, everyone is into Formula One, and I'm like, I'm so happy that this happened. This massively increased my quality of, at least my Monday morning discussion. at work. So anyway, then I'm on track for position, maybe newer tires and the people in front of me, so I'm gaining a little bit. When I come around the corner and I see that there's two, there's not one car for position, there's two cars and they are fighting, and now I'm going to overtake them both. They use this. It's just like you lose a lot of time than you're fighting with someone directly. And so I think that's like that's the difference. I mean, were you able to, this sounds like learned experience to me. So I'm curious when you started your Shopify venture, maybe even your snowboarding venture. I mean, did you, did you, is that how you thought, or were you looking for editors?

I, I oddly grew up. So like, again, growing up with computers in the 90s, like, I know this sounds weird to make this analogy, but like, like you're familiar with open source software, right? Like purely sharing, like you build something, you shared, there's massive open source projects, Linux kernels, these kind of things. The open source, open source is fundamentally positive sum. No one loses by someone else making a copy because in the world of computers everything is infinitely copyable just for the price of electricity, I assume, which is essentially free. The real world is often much more rivalous, like only one person can live in the house or on a spot or only one person can have a physical object, but in the digital world

there is actually two positive sum. So I think because of that, I was a bit of a bit of a bit of a predisposed towards positive sum thinking because I've just seen it more in my title. So, you know, when you are creating a business, you're, like, you're not competing with everyone else, like, in that same space. Like, you can very much grow the space, because you bring something new. Like, the way we talked about our snowboards, it's just totally different. Everyone else had, like, a grid with, like, many snowboards and pictures and a prize, we had essays about what we did with a snowboard

throughout the day. We just took them to a mountain and then said what happened that day, basically. And it's like sometimes it wasn't even quite related to the snowboard itself. But that spoke to a new group of people who might not have bought a snowboard at all if it wasn't like this,

or might not have purchased such a premium snowboard. So there's a growing market for more people growing market for more people aspect in this, which I always really, really try to emphasize. So, but you're right that it's somewhat learned. So what happened is by 2015, so this is 10 years in the company's history. I don't think we truly had competition. more for exact business, sort of in the enterprise business that is like some players. But there was no one going for the small and medium business market.

In fact, even really along the way, there wasn't, like, it just, everyone deemed it as a terrible market to go after. And that was sort of a surprising thing. It never seemed like this to me, but like, I'll tell you, like, I, you know, in 2008, I was needed, like we were running, I had to hire some people, right? Like I had some support at Shopifycom, at some point needed to not just make it to me, right? Like I needed to hire some people. They were like eight or something in 2008, eight people.

And we made some money and I still had some savings from Snowdevil, but like I wasn't taking a salary and we were just living with my in-laws in their house. and Fiona and I. And so we kept cost down and it was hard to meet payroll. I wasn't spent to Silicon Valley finally and just start fundraising. So I wanted to like, you know, I had learned how to do all this and I did have a pitch deck and so on. You know, ultimately, people passed for one reason or another, on the company. And very important, big venture capital firm that everyone would recognize passed on the

shop of ideal. And years later, I met with the partners again. And Pana asked, like, hey, Toby, like, what did we miss? You know, I was like, you know, reminded, like, you passed because you decide for yourself that there's like a global market for 40,000 online stores, right? Like, this is sort of the internet at the time in 2008, there's 40,000. And if Shopify is successful, it might get 50% of a market. That's like, that's still not enough to business to justify

a valuation which would have been very low. So what did we miss? Okay, here's what they missed is that Shopify itself was a solution to the very problem that they stated. There was only 40,000 online stores because no one made it easy to start them. Like the only online stores that existed, they were already rich businesses that had the $25,000 or $250,000 to make a web presence and build an online store and like they were all attached to existing businesses

that are already rich, no one built for the new entrepreneurs. And so Shopify grew its market instead of competing for percentage in a market. And I think that is like a very, very, very different thing. I mean, so you started this roughly in 2004. I mean, I feel like there were competitors of your yours back then. I mean, I remember GoDaddy was the first, was the first one that I tried to build a website myself on GoDaddy. I didn't, I did it, look like shit, and that's when I was

like, all right, I need a web guy, a website builder development guy. And then, you know, but there were other things that came along the way, I think maybe Wix. Shopify is not a unique idea at all. Like, it's like, in fact, it's one of the most, I mean, There's hundreds of companies that have and do ostensibly the same thing. The technology industry is never about who does something first. It's always about who does something right, which is what makes it so interesting. All the commerce companies of that time, even if they started wanting to service new builds entrepreneurs, always fled up market because they have been.

had a lot of money. They serviced existing business and could make way more money. It was expensive to deal with small businesses. The general advice that I got when I asked around was just use eBay. Like, start your business on eBay. If it works, then talk to a company called, the one I got recommended was Miva Merchant, which would then take a lot of money to build an online store because now I have enough money to give it to them. And then you would we platform again afterwards and it's it was like specifically for the new entrance I'm not aware of anyone making that specific goal it might but doesn't mean it didn't exist and no one did it there was one the closest analogy was a

thing called Yahoo stores which actually Paul Graham started with an interesting character his own variety started Y Combinator later and which of course became the origin source for so many of the tech industry's greatest companies now. But his original project was a thing that got purchased by a company called Yahoo! And then turned in the Yahoo stores. I tried to use that and could not make it work. You've probably seen the headlines. Another trillion added to the national debt.

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You'll learn how to help safeguard what you've worked hard for. Plus, you could qualify for up to 10% in free bonus silver, one of the best deals out there. So visit shonlikesgold.com today. One more time, that's shonlikesgold.com. Performance may vary. You should always consult your financial and tax professional. I mean, what did it do? So when you entered this, the competition thing just I fucking love what you're saying. I just, I'm trying to, I just want to know, like, when did you, when were you able to totally detach yourself from the competition?

And I feel like with my business Germany, I'm just now arriving. there i wish i would have arrived there a lot earlier because i because i also see that it it's a time suck it's a rabbit hole that you can go down and spend a lot of time discussing competition with the team and it yeah it it's a it's a subject that never ends right and so i'm um i'm like right at the point where i'm starting to detach like i don't give a fuck about what anybody else is doing and i think part of the reason that that's happening is because we are launching other businesses in 2026. And that is, I mean, the show will always be my staple and I'll love it and da-da-da-da-da. But, you know, if I'm being

perfectly honest, I'm more excited about a tech company called Glacier that we're launching in 2026. And that is taking my brain out of, it is detaching my brain from competition with than the podcast world, which is more bandwidth in my head to build more things to become more successful, is what I'm saying. Exactly, and I mean, again, back to my analogy of the tree, I mean, the podcast and the community built from it is the trunk, and you can now fill out the tree

with more branches, right, like that are part of it. So again, and therefore, you end up creating something that is not a direct analogy. analogous has no other that are doing the same thing. It's like now it's like unique, it becomes an oak, right? And I think that it's better to build something that's like a unique construct. It's okay that this happened just one step at a time and didn't come from some kind of crazy business plan ahead of time. In fact, I think the best businesses tend to be the kinds of businesses that would lose at every.

at every business plan competition, funny enough. And I mean, again, like my company itself started like this. It's like a snowballed store to e-commerce software to really what is Shopify's retail operating system, I suppose, now, but it's so many things. The comment on the we didn't have competition, I feel like I should put some meat on that bone because it's, again, Obviously not true that there aren't other e-commerce companies and so on. But what happened is, I think we learned what we could learn from them.

And again, I do think it's very valuable to talk about competition, but always from a perspective of what can we learn from them. What have they figured out? How do they uniquely handle their particular challenges? Because we're looking at the same problem space and find different solutions. And so in a way they can act as to fill in the blanks. The paths you didn't travel. You can now see, well, they made a completely different decision,

solving a current problem. At some point in the 10 years after we launched, mobile phones become more important than the desktop browser. But the entire internet was built for the desktop browser. And suddenly all the sales were mobile, like every company in the space had to react to this. Some of them didn't, and that told you a lot. Some of them said, OK, well, we give a completely different

interface to all mobile phones, like as a sort of companion system. You have your own brand on your own website, but if someone uses a mobile phone, you see the thing that our team created. To me, that seemed like incredibly wrong, because, again, the beautiful thing about shop, again is almost everyone who's on the podcast has used Shopify probably recently.

I mean, especially you're the customers. You just don't know it, right? Because if you bought something online and didn't come from Amazon and you like the experience, it was probably Shopify, we are not the brand. We are pushing from behind, we're pushing other people's brands from behind. So therefore, this is an article of sovereignty. What is onable on the internet? There's two things that you can own.

There's your domain and what's behind it, and there's your email list. Everything else is rented. Everything else is leased from others, like your Facebook pages. Depends on Facebook how much reach that has and so on. That's not a bad thing. is. If you're selling through Etsy or so, that is also very good, but it is Etsy's listing. And Etsy will determine if your products show up for a search query or not. But on your own website, that is your space. You're gaining sovereignty there. You can take

that entire design that you have and take it with you wherever you go. You can get all the data from Shopify. This is super important to us. So then the mobile phone comes out, it's your job. We have to figure out how to make it so that your brand looks just as amazing on mobile phones as it does on desktop software, and that's what they helped everyone with, and that ended up being the right decision, just as an example in this. So again, looking at the competition from a perspective, what can we learn from it, and can we have a friendly rivalry with them, then has always looked really well.

Eventually, and here's the reason why to do this. It makes everything else easier to have an enemy. That is true. It's much, much, much easier to say, hey, this other company wants us dead, therefore we need to work really hard. Because everything else sounds hollow. It's like, hey, everyone, let's work really hard because reasons. Did you, did you, I'm curious, did you use that to drive your team? So I ran out of credible things to point at, at some point.

And so this is why I talk about intrinsic motivation a lot, because I had to think about it a lot. How do you create an intrinsically motivated company to where everyone works really, really, really hard when they technically probably don't help? have to right now. Like, you can talk about the future competitive might come out of the woodworks that does everything better.

And of course, companies constantly get disrupted because they become lazy and fat. But what the way to, like, the only way I found is to, for people to fall in love with the mission. And the mission is to make just like, make more entrepreneurship happen, make entrepreneurship more more tractable, make our customers more successful. And know that if we fail to, if Shopify isn't a representation of a sum total of our skills and beliefs in what we know how to build the best possible e-commerce software at this moment, more people will fail, right?

Because this is what we see over and over in the data. Every time there's an area that makes people give up in their entrepreneurial journey. If we then find a way to significantly make this easier, it's the people who otherwise would have given up make it. It's entrepreneurship stops via hurdles. And it's when some people at some point in some emotional state are too encumbered by self-doubt or the stresses of building a company and they encounter some kind of thing that has stumped them.

And if they're in a wrong mindset, they might go. called quits at this moment. And if the obstacle wouldn't have happened, you know what it's like to be an entrepreneur. It's a roller course, so it's ups and downs. It's like valleys and peaks over and over again. And sometimes in the valleys, it gets pretty close, right? Like there's pretty dark days in any one's entrepreneurial journey. So again, I think falling in love with the mission or

at least allowing, like, at least falling in love with being on a mission with people you really care about, doing difficult things for worthy people, is an incredibly fun thing to do. In fact, I think it's kind of an optimal way to spend your life, really. And I think we've succeeded significantly. Today we have plenty of competition. I'm not going to say we don't, we have no competition left. It's like it all came back and it's like, again, much more easy to study what other people

doing AI is like changing everything and there's not a company that's safe in the world and I love it. It's so much easier. It's so much better. It's so much more fun. It's so much more creative. It's so much more driven. I mean I get to like I saw many transitions in my career in of the technology world. I saw the internet arrive basically. I saw web tool, which, whatever that is, I saw, you know, like the mobile phone coming and now what happened with AI is just like another platform. Like usually people should be enormously lucky to see one transition of a platform in their careers.

Like four in now. And it's unbelievable how exciting this is to have to invent everything. I mean, I want to move in, I mean, since you brought up AI, I would love to talk about, you know, what you think that looks like and are we at the, I mean, is this as big as the invention of the wheel or the invention of electricity? But before we go into that, I just, you know, one thing that just talking to you now that comes to my mind is obviously probably one of the best engineers, I mean, in the world. world. And, you know, what I'm, what I'm, I'm not trying to blow smoke right now. What I'm getting at is, you know, what, what, what, what drew me to Shopify is how you were able to simplify everything on the platform for a dummy like me. So, I mean, some of the things that took out to me, for example, I've always, you know, it was always like, how do I connect my social

media to my website. At the time, that was really important to me. And these web developers, you know, that's going to be another $10,000 to make that, you know, connect that. I pull up Shopify, and I'll never forget it, because that was such a headache for me. I was like, I really want,

I need social connected to the website. And I remember building the website and seeing, do you want to connect your Instagram account to your Shopify store? Click this button. And I was like, are you fucking serious, man. This is so, this is easier than putting a PowerPoint together. It's prompting me to do the shit that I've always wanted to do. And so, you know, kind of what I'm getting at is

if you take a complicated mind, you know, you're very into this. You're way more advanced than 99.9% of people in the world when it comes to, you know, building this stuff. How are you able to get you and your team, how are you able to dub it down and know what basic green entrepreneurs need, you know, in building their website? I mean, to go that granular, you know, from that advanced of a mind is just, it's honestly, it's pretty mind-boggling. Well, but it's easy. Like, it's, like, you talk to them a lot.

Like, I mean, I, son, it's Monday. Monday now, right? Sunday evening I watch videos of people using, like interviews of people and recordings of new entrepreneurs using Shopify that our, you know, teams create. And it's lovely, right? Like, you would, like, you, you, like, I have, like, I'm like, in, you know, like 150, my of my customers in WhatsApp, right? who will tell me, like, Shopify is collaboratively created with our customers, right? Because again, the best, like, if I want to grow my business, what I need to do is make my customers more successful.

And that's like, it's very rare to have a company that's so aligned with its actual customers. And that's, and also one of the funniest that one of the funniest this company has is, like, that there's very few companies on planet Earth who have such inspiring customers. I mean, you go on custom, you're pretty inspiring. Yeah, I mean, so hold on. Let me just, so you are going, you are watching video, interviews of your customers every Sunday. Yeah. I mean, I'm just going to bring another thing up.

One, I got to thank Lulu for connecting us. But, I mean, we just released our SciOps docu series on Shopify. And I'm going to be honest, like, when we reached out, I thought we were getting the special treatment because, of our mutual connection, Lulu, and maybe because it's a big podcast. I thought we were getting special treatment, but after hearing, and I appreciate that, thank you, because nobody else could launch the docu-series. It's on Shopify. I think we're the first ones to be able to do it, and it's because your team jumped through hoops.

But, and thank you. But this, so that's not like a, that's not a special thing. Like you, this is what you guys do. You get in touch with the customer, with the entrepreneurs, and you figure out what they need and you do this every Sunday. Yeah, I mean, it's, I mean, I don't do it every Sunday, but as many Sundays as I can. Like, it's, it's my team, like, makes super cuts of the interviews we do

and sends them to me. So, like, I can see what, like, how people get stuck and so on. But, like, because, and I use Shopify, I use myself, right? Like, I'm a user, my, I always have shops going, and I sign up for new shops and, like, go for onboarding, and talk to customer support from pseudonyms. And it's just like, I'm like, I'm red-teaming my own company all the time, right? Like, so I'm a pain they asked to work for because of that,

but like it's also like, that's kind of what you need to do when you're trying to, like, look, as a CEO and founder of a company, it's dangerous to get disconnected from a product. Right? Like, it's pay, people like get really, really, really good at telling you a combination of words that makes you look elsewhere. I've had plenty of such experience in my career. And so, you know, be in all the details is important. I review every single project that's going on with the company every six weeks. And it takes 12 days, usually three days.

We go through every single project. We have an entire system. an entire piece of software for that everyone uses to, that we build, where everyone registers everything that's going on. In fact, that was largely inspired by military, actually, a book called Team of Teams by General McChrystal, which is excellent read anyway. So we built an internal system that sort of asynchronous distributed. information system about what our teams are working on,

all the projects, progress updates, who's on them. And then this bubbles up into a six-figure review, and then we go through them, and I have a super, like, sometimes a quick, but like the team is there. We can quickly talk about how things are going, what's stuck, and then keep going. And then we move, try to move all the these projects to build everything we can in such a way that it works well with everything else.

And this is, I have, I don't think this is the only way to build software at this scale, but it's certainly the only one I have discovered that is, that allows us to build a software like Shopify at this scale. And because automatically what you're trying to accomplish is you want people to use it. And I believe that every user of every piece of software of every product in the world can intuitively tell you if a team that creates it did give a shit about the product. I think this is just known to us. It's like it's invisible and we don't have good language.

But I think everyone can tell. And so, well, if you want to build a product that people would answer this question in the affirmative, you have to give a lot of shit. There's a lot of shit has to begin about the tiniest of details, about minute architecture, the chunkiness of the buttons of the design systems and stuff like this that no one, like, it would be so funny. I mean, I guess this is why the Silicon Valley show and HBO was so funny, then when people who are in their tech industry kind of get exposed to the shit that we discuss

and have discussions and meetings about, right? It's like ridiculous. Yeah. But like, unfortunately, this is what it takes. So yeah, so we go through everything and we talk to customers and why? Look, like, I mean, I don't want to criticize you. Where did you learn that? Where did you learn to reach out to your customers?

Oh. It seems like the most successful tech entrepreneurs in the world have all have a grasp of this concept. And there's a whole hell of a lot of people that have no grasp of this concept. But I mean, where did you, I mean, when did that, how did you figure that out? Yeah, it's, it's, well, I mean, I was a customer support initially, right? Like, so I did it because I had to, and then I could hire people for doing it. And at some point along the line, I started making choices that weren't right, because my sort of inner model of what an entrepreneur goes through when using myself,

it was just like starting to be dated. And I'm like, well, I have to figure out a way to be more connected. And, you know, I did, actually haven't done this in a few years now, but like until like a few years ago, I did like actually an afternoon in customer support, you know, just like maybe once a quarter, once a half year or so. And it was always very good for me, just very humbling experience too. you know, actually help people, especially at their vulnerable time when they're confused. They call because for a reason, right? They call because something is really important happening and they need help, right? So, I don't know, you need empathy for the people using the software. And I don't know if I, yeah, I just came back to

doing it this way. Here's my strongest belief that I was cringe a little bit when people say, like, sort of people have, like, clearly a bit of, I hear this a lot when people say, I don't know computers or not technical or so. Well, no one's supposed to be technical. Like, the whole thing that people have to be technical to use technology is because of skills issues of people like me, right? Like, it's completely unfair. And, like, you don't have to be technical to use a television. You have to, like, turn it on and you go to the channel, right? So that's the engineers and product designer doing a good job with a medium.

But, like, if you were better, no one would ever feel like they can't figure out something. Like, computers don't get to make people feel dumb. That is not their role. They are tools. like hammers don't make people feel dumb, you know, like school drivers don't make people feel dumb. We have the only field, the only field of tooling, support and infrastructure that somehow is allowed to make humans feel not good about themselves somehow.

And it's just normalized. What we actually should do is give people superpowers, because that's what it does to us, like to us the engineers, to us the technical, people, computers. The way I talk about computers will be clearly very different from how most people talk about. Why? Because I do love them for what they can do. They are incredible. But to get this, the power that I can extract out of a computer, again, I had to sacrifice my youth. It's like path-dependent. for people who for unexplained reasons wanted to cultivate rare but valuable skills around computer programming and understand them at like an intrinsic level.

And those people can experience them as the incredible most powerful tools that you may ever come invented. But everyone else should do that too. And so I think, luckily, I think now with AI we're getting this. This is the best thing about AI is we kind of get a do-over. But there's too many stories of people feeling inadequate, not being able to accomplish their tasks because we just cannot make software that meets people where they are. So no matter how hard I work and my team's work, it's never going to be enough to really

get all the way there because it's just like unfortunately there limits. But again, every single time someone doesn't end up giving up on an entrepreneurial journey means there's one more business that's going to supply employment, supply, I think it's just like that someone else becomes an entrepreneur in the eye of their own children, grandchildren, family. And again, I think it's an identity changing event. And so it's important. It just feels really, really, really, really meaningful to be able.

to work on something like this. It is. It's up. I can't even imagine how many lives it's transformed and put on a higher trajectory than what they were. But moving into AI, a little rabbit hole here, I've been, you know, a lot of people are worried about AI. We've talked a lot about it on the show.

You know, people are worried that's going to take their job. Probably is going to take a lot of jobs. It's also going to make things a lot easier. I'm curious, as to your thoughts, I mean, are we had something that is Is this as big as the invention of electricity or the invention of the wheel or the invention of the internet? I think so. This changes the entire way of life in the next five to ten years.

It does. It really, I know this is going to sound crazy and scary and probably will be quoted back at me at various times when people are somewhat down on AI. But I just think AI is actually underhyped right now and that seems almost hard to believe I know it's just it's it's you think it's under hype I think it's under hype wow it's for all the hype that's already exists it's all it's still underhyped and what it can do it's just like our ability to project intelligence at problems without losing um without having to allocate

some of our, like, rarest and most specialized people to everyday problems is just huge. It's so easy to run into examples here, but, like, I'm getting so many stories right now from family members and friends who are solving, like, really, really, really tough medical problems for them that they couldn't solve. And they've done all the right things. they have done every test, they've talked, they've gotten second opinions, they've described, they came prepared to every doctor meeting, but then, you know, at some point they just start one of these projects on chat GBT or whatever and put all of this in there and then just like

let it go into deep research on this. Like again, this is something you have to be comfortable of data and all these kind of things and maybe like people do it anyway. And it just sort of figures out what's actually going on in a way that you can show up to the next doctor and just finally get the thing that you were looking for. And why does this work? It's not because it's smarter than the doctor. The doctors are way smarter, way better. But the doctor only has 15 minutes to sit down with you. They have 15 minutes, maybe 20 to look at the charts.

talk to you, get information, and, you know, 20 minutes of a doctor's time is probably with hours of an AI doing something right now, but I can put thousands of hours in, and some tasks just benefit from just intelligence being projected into this directory over a long period of time and can be solved. And I think that's a lot of things, but it's usually tasks. It's like, here's the task of taking the information that has been collected, you know, all the scans and all the reports and all these kind of things. And sift through them, go through all the literature, figure out the latest developments, you know, compare and contrast it with all the medications that have already been used and the reports about, you know, just like this is, it's just a thing that humans could do. but like we just don't have enough people for doing this.

And so I think just like that alone changes the world in a way, right? And so it turns out that it's true that jobs will change, although much, this always gets into a really, like everyone has sort of a different question and different jobs in mind. I think what AI really does is it outmites tasks and it allows more people to work like you and I, because, like, we have teams for, like, if we need something, research, we have people we can email and they will research it for us, right, like, and send us back a report. And I think more people should, like, should have ability to have something like this.

And frankly, you know, sometimes it just speed matters. Getting something back in, like, a minute actually allows you to, like, it might not be as good, but like you can then make modifications and ask it again and like help yourself figure yourself out. So I think it's all this stuff is pretty remarkable. But yeah, it's where I am most excited about with AI right now is just we see this. So the thing I spend more time on than anything else on at Shopify over the last couple of years is how to integrate a helpful AI into Shopify the software, right because for exactly the things we've just been talking about i do never like i i see it as a personal failure and it's almost physically painful for me when uh when when um especially my

software makes people feel uh inadequate um i want my software to inspire people and make them more ambitious when they always would be i'm not um less and um so i AI. Like, we have this is integrated in a shop for it's called Sidekick. Having a, you know, infinitely patient, extremely knowledgeable, you know, kind, non-judgmental AI sidekick as part of your entrepreneurial journey is extremely game-changing from our perspective. This exists, this is a Integrating Shopify, everyone gets access to it. And the conversations people have with their tell us are just like, it's remarkable.

Like, you know, the big businesses ask it to run reports. The new entrepreneurs ask, like, where do I have to go in Minneapolis to register my business? You know, it's like, how do I open a bank account? How, you know, like, it's all the kind of questions. That's going to be embedded inside a Shopify? It already is. it's hundreds of thousands of people are using it daily.

It's just like, it's like, in fact, you can't ask it to do jobs for you. You can say, hey, here's my, here's, I got the, I got a PDF here of my supplier for the summer collection of products. Can you please create the products and add them? And, you know, just, it will go and do it. And it's like, I hope it's doing a great job doing it. Like, it probably might, it might get some things wrong, so you will definitely show you a review screen for everything, but it's increasingly

able to just join your team as a team member, right? And again, especially for the solo entrepreneurs, that is an incredible change because now they have, I mean, a team of one, like that's cool. Wow, they literally have an assistant. Yeah, they have an assistant. Holy shit, I can't wait. I've got to go ask my guys if we're using this. Yeah, you should check it out.

It's fun to have conversations with. I really, I'm super biased here, but I'm a really, really big fan of this. Again, most of the intelligence there comes from the wonderful advances of labs like opening Ironthropic and others. But, like, you know, Shephy is a bridge company fundamentally. We are a bridge between the world of, the global world of commerce. And the technology world, like our job is to go and get the best things that the technology industry can do and make them available for people who are trying to self-actualize, right? Like, this is our native habitat. And so that power that we are getting for helping people with AI in doing this and what we can deliver to the people who are just,

going to sign up tonight for in trying to build a business is just like absolutely remarkable and this is why i say it's still underhyped that's amazing that is um wow that's incredible let's take a quick break uh when we come back i'd like to talk about um how you run your team i know you run it lean and uh would like to just move into that so good My days don't slow down. Between work, the gym, and time with the kids, I need eyewear that can keep up with everything I've got going on. And that's why I trust Roca. I've tried plenty of shades before, but these stand out. They're built for performance without sacrificing style. I've put them through it all on the range, out on the water, and off-road. They don't quit. They're lightweight, stay locked in place, and are tough enough to handle whatever. I throw at them. And the best part, they don't just perform, they look incredible. Sleak, modern, and designed for people who expect more from their eyewear. No fluff, no gimmicks, just premium frames that deliver every single time. And that's why Roca is what I grab when I'm

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That's ROKA.com. All right, Toby, we're back from the best. break, we were getting ready to dive into how you run your team. So I've, I, you know, I was picking through your outline and saw that you'd like to run small and lean teams. It doesn't. And this is, this is, this is a growing pain that I'm trying to figure out right now. If we want to go and we want to bring everything in house, which is kind of originally what I thought I wanted to do at the beginning of the year. And now I'm starting to think, I don't know if I like all these people running around and I don't want to get, I don't really want to get any

bigger and deal. I like to keep, I think the way I'm going is I like to keep my internal team extremely small and lean and nimble and then start to outsource more and more to other companies, not individuals, because I think companies might hopefully care more about their reputation than what I have been dealing with. So anyways, I want to, I'll just want to get your thoughts on that. I mean, yeah, I mean, at the end of the day, like, everything is about the team. Like, a company is actually not a thing, really, if you think about it. A company is like a collection of individuals that we just call a company. Every company is getting, like a company can't gain something.

skills by itself. It's just the individuals in the company might develop a skill or you might bring someone new to gain a new skill. So it's kind of like, honestly, the beautiful thing about companies is that they get to align a lot of people's incentives all in the same direction and then everyone gets to, you know, spend their day together doing hard things, hopefully, unique things and so on, so on. Reality is there's a huge amount. complexity and just getting these incentives alike, right? Like it's so often that lots of people just like end up like sort of grinding against each other and like all the energy is sort of diffused by the grinding noise they make and

by just like being in each other's way. And the solution to this is like, I mean it's like one of two things, right? It's like it's either you drive people towards making a consensus decision like or there's going to be leadership and those things are kind of opposite. And I don't think that's a commonly helped leave. So how do you set this up? I mean, I'm a big fan of small teams. I think small teams in general are, I mean, the best-sized team is one person.

That's just like anything that one single person can do should be done by one single person. because, you know, like, that requires zero coordination. It's like you sort of in your head, you can consult. Like if you have all the skills to do something, then you don't need to coordinate with anyone. Books tend to be so good because they're written by one person, but usually with an editor. So now you have one person holding the pen and being able to construct an incredible fantasy world with all these characters and, like, perfectly. like everything written in the same tone of voice,

the characters act consistent to previous chapters and so on and so on. If you would give every chapter to another team member and write a book, there would be no cohesion between these kind of things. So, like, especially if you don't actually, if you try to do it all at the same time, because then no one can coordinate, no one knows if, you know, who Bob really is. Bob shows up in one chapter, different from a chapter,

other chapter. A lot of companies, unfortunately, run like this and just try to, like, write a book by accelerating it in such a way that they puzzle out the tasks and give them to a bunch of people, and then you end up with kind of a mess. So at a certain size, when a task is bigger than a book, you can't do it at one person anymore. And now you do need a team. So, but you should understand, like, every single time, like, if you do this, you are still trying to create something that feels to the people who are gaining, like, one other side, like the product needs to feel like it was written by a single offer, even though you had, in our case, like three and a half thousand engineers building the thing.

So that requires an enormous communication challenge, which isn't to be underestimated. The second best size of a team is five with an ability to flex to up to eight for short period of time. But it needs to be temporary. That's what we found. It seems like that military came pretty much to a similar conclusion, right, like in sport sizes. I am not a military export, but it certainly seems that way. I found that these teams, like I think parceling things into teams that fit that mold, that size is the best, as long as you have a clear person who plays a role of editor.

And someone who kind of knows what overall needs to be produced, how to make decisions, someone who can be escalated to if two teams disagree on something, and who can help with coordination. That's basically what the six-week reviews do at the global level, and then I work with lots of others who hold the editing pen in other areas, at smaller levels. I don't know if that specifically answers your question, but I think what I've found is there's a lot of myths around that really, really are in people's ways. And I think this is why a lot of scaling of small companies ends up growing poorly. I have a pretty controversial take on this.

I think part of the reason why there's so many myths about teams and are on, it's because only people who have time to write books are sort of middle managers. It's not really the people who actually ended up making the difference or having the leadership position that truly end up writing the books. usually the books are written by middle managers who ended up being in some industry that was just experiencing rapid growth for extrinsic reasons like telecom like like the telecom industry in the in the 2000s like nine then for a half a century of mega growth it was like it started out it's called

hundred million a billion size of industry went to multiple trillions just because of demand, right? So if you had a pulse, whatever you were part of grew a lot, probably despite of everything you ever did. And then people make a lot of money and then retire and then write a book about their pet theories about how they did it. And that's what everyone studies in business schools. And it just is completely independent of what actually matters.

So things like don't micromanage. is one of those things. No, micromatch. Like, it's crazy to not, like, not micromanaging is an insane idea. Like, you gotta be in the details. Like, don't micromatge if you don't know what you're doing. Like, don't do the things that make your team do worse than what they otherwise could do by themselves. But always be there to help them do better if you can. Right. So, but like you find so many people who are like, oh, I don't want to be a micromanager, but like, you guys are basically barreling down in this car at 200 miles an hour going over a cliff that you just can't see yet and I know, I have a map and I know it's there. No, like just like actually have them drive around that thing, like that's a good idea. And so that's, you know, that's one of those kind of things. I got myself in a lot of trouble with just sort of getting out of the details for a while because I've thought I need to become, you know, I'm running a public company now.

I need to be CEO, like, I don't know, from central casting. I need to trust but verify and, or not even verify, just trust, trust faults everywhere. And it's like, that's fine, but like, it just doesn't lead to, like, eventually people will know what combination of words causes trust and everyone's allowed to be an intelligent an actor in their local incentive system. So if you can basically do whatever you want, as long as you just use a particular way of explaining it, you will. Because that's expedient.

And so eventually things that go poorly. What I've found with my direct teams is I want people who have some strong specialization in something. Usually come, it might be the law as background, or might be an engineering background or design or anything. Like, I want to work with people who have, like, been clearly excellent at something and then spend time adding more skills, like building range and perspective. I want everyone in the team to be able to put, like, at least in theory, do a reasonably good job switching roles with others in my executive team. And I want people to be able to be.

be as little beholden to orthodoxy as possible. In fact, I actually require for all my team members and leaders that at least once a year they go to some international conference or maybe a podcast and talk about how they do their area of a business differently from how other people do and therefore better. That's a good topic for me to talk with them about in a one-on-one, but also just keeps them thinking about, you know, what opportunities do we have to do things better? Because nothing is ideal in companies. We are not actually very good at building companies at this point in day and age.

It's understudied as a field. And then through these conversations, I try to build trust with them and make this an actual thing we talk about. We talk about trust as a battery, essentially. It's something that you charge over time with every interaction. like we do something together, you solve a problem, or you say what you do the thing that you said you would.

That's a small charge on a trust. And then, I don't know, like you show up late for every single meeting or you kind of phone in on, you know, slides for whatever, whatever. It loses some trust. And so I found it very helpful to just go and like, hey, here's like the things that added some trust and here's the things that you lost some, so we're kind of even right now.

and if you just eliminate the ones that lose trust. You say this? Yeah, I say that. You're very direct. I'm very direct. That's how I am. I'm German. So I'm like, it would be odd if I'm not direct, so it might as well lean into the stereotype.

I speak direct like this. It can, um, it's not always received the greatest. I'll say that, but I like to speak direct because I've, you know, is uncomfortable as it can be to speak direct. if you don't get lost in the conversation it's very precise communications it's this is what we need done this is don't do this again this is why let's brush the shit under the table and move i like to speak like that i get a um feedback that i can be unapproachable intimidating um i have very high expectations which i've always had very high expectations. I mean, I grew up in the fucking SEAL teams, and then I went to the CIA, and then I built a company. And, you know, and everybody that's here right now, I think, understands, like, yeah, Sean has extremely fucking high expectations. People that don't understand that don't last

here a night, you know, but, you know, and I think it can be, like you had mentioned, I can be a pain in the ass to work for. I can be a pain in the ass to work for. I have extremely high expectations. And, you know, but we wouldn't be where we are today if I didn't have extremely high fucking expectations. We would just be like any other mediocre fucking podcast, mediocre company. And so when I hear that, like, oh, Sean has high expectations. Yeah, I do have fucking high expectations because I want to be the fucking best. And if you don't want to be the best, then get the fuck out of here. Exactly.

Like, is that how you run yours? You have to make it clear. I think the only problem in this entire story that I've heard is the people who can't do it want last year, figure out how to make them not even show up. Make this more obvious. And it's funny how hard this is for companies, because there's this sort of belief that every company should be absolutely for everyone. No, that's, like, not right.

Like, companies, we want diversity in companies. We want there to be a... that's excellent for people that it's excellent for. And not, like, you know, if you take everyone's favorite color and blend them together, you end up with mud brown which no one likes. And we have enough mud brown companies, right? So, you know, some people want something different out of their career. They want to work hard on worthwhile challenges for worthwhile people.

And I think the earlier, as you said, the more you heightened the misalignment with the people who just, who just probably wouldn't, shouldn't be joining, the better things go. And so it's actually, it's an unkind lie to obscure this, if those are the expectations. And these expectations, the high expectations and the exacting standards and the, hey, we are building something unique and that is uncomfortable what we are, all that is 100% lot-bearing for the success. There is no chance. This is a accidental success that happens to have these sort of downsides of high expectations along the way.

And because of this, it was harder than it otherwise would have. But like, now that we have arrived somewhere we can stop having these expectations, no, fuck, they are the reason why everyone is there. And everyone who wants to work for you wants to work for you because that was part of a story. And if not, then it's not going to work. And it's actually kind of an unkind to not tell people early because they might, you know, our careers are not that long and people should like only work for places where they can be one of a, they have a potential to be one of the top performers at. And if we already figured out in recruiting, but like,

yeah, probably not going to be one of the top people who are probably not going to be one of the top people or probably isn't what they are going for, but, like, there'd be a solely contributor. Yeah, that's miserable. Like, someone who's a mediocre performer at your podcast, would they likely be absolutely badass somewhere else. So let them go be top performer somewhere else. I think that's a hard one lesson.

And it's, you know, maybe even an unpopular thing, but it's also just kind of true. And as they say, truth doesn't care about everyone's feelings, so it's better to explain this. I mean, I see, thank you for that. I can, I mean, I can tell that, I mean, it's very obvious that entrepreneurship is, you are very gung-ho about that. You want, I mean, that's the whole reason, you know, you started Shopify as to jet launch entrepreneurs. And, you know, just through our discussion, I can tell you, you know, you've found a lot of

freedom and I have too and in entrepreneurship and it sounds like you think there's no better time to become an entrepreneur with everything that's going on in the in the world right now and and so you know why why is now the time to become an entrepreneur it's I think it's the perfect storm right now of where like individuals and small teams have more ability to do greater and greater things than at any other time. You know, if, I don't know, this is really absurd, but like, if you look at a sort of global GDP through all time, there's charts for this.

Like, I think our world and data is a great website which has these kind of things. You can look at from, like, Christ's time. You had, like, for 2,000 years GDP on Planet Earth. is exactly a map for how many people were on planet Earth. The only way to create productivity, if you will, which is what GDP measures. And of course, these are approximated numbers

because no one actually reported GDP in 800s. But the only time productivity on planet Earth end up is when a person was born or then a piece of burden was added. And so then we have Industrial Revolution. We figured out how to use steam to make kinetic energy and then electricity. And suddenly these things decoubled. Suddenly we could use kinetic energy to make things. We could make factories and steel and railroads and all these kind of things.

And wealth in the world due to productivity just massively increased. This is where everything we like about the world, about the economies we have, about the external of living, about how many people they can keep alive. All this stuff happens because of this one moment. And now we have another thing that we put on top, because it's not just kinetic energy, we can also project intelligence into worthwhile tasks in a loop forever until they're fixed,

or until now they're not fixable. So because of that, we... we now have, like, a small group of people are not, like, only have the skills that they show up with. They also have, not a work class, but a, you know, like, if a best person, if a best program in a world, it's a ten of ten programmer. Like, every team, every individual on planet Earth currently has access to a six out of ten programmer as well. and a six out of ten designer, and a six out of ten entrepreneurial advisor, and a six out of ten lawyer. Now, there's a lot you can do with this. And so it's a great, it's just a glorious moment for more people to reach for independence

because we are at the beginning of something and there's leverage in doing it. And also, because I also just almost want to persuade people to try it because I think one of the best versions of the future is one where many more people are active participants and put something out there again. Like, we need more people to create products and services that other people find valuable. Like, we are just like, the amount of new businesses being created has been declining for a very, very long time.

No kidding. It's been a leaky bucket. It's like every generation has been slightly less entrepreneurial than the previous ones for ever since the baby boomers. Is this throughout the world? Throughout the West, yes. It's recently starts leveling out again.

It's just, it's cresting, and even in some countries there's been more new business formation again, which is really, really hopeful. Now, there's a school of thought that says, well, this is because people are losing their job. And it is true that one thing that happens when people do lose their job is sometimes they make their plans. Plan B, they knew Plan A, right? Like, lots of people are like, I've been sitting on an idea. I wasn't looking for doing this right now, but I have an opportunity, so I'm going to make a go at this. We saw this a lot in previous, like, financial crisis of Lehman Brothers this, like, time. We thought we were dead when this started happening, but it actually turned out that more and more people were starting to build businesses on Shopify, and we could help a lot of people.

a lot of people are there in these times and doing COVID again. So it is a time where people should have a plan B in mind and see if there's an opportunity to make this plan A. And they can access so much more help than before. And so I'm very, very bullish on this. Do you have any thoughts on renting versus owning? I think both. I don't want to make a moral judgment.

I just think it's like on these things, because it kind of can veer into that territory. Otherwise, I think you should definitely own something. There needs to be a home base that you can fall back to, like some base camp for you which no one can take away. It's very good. The, and with, like, I mean, you know, people are generally more ready to improve, you know, you know, do home improvements on the house they own than when they're renting. And I think all the same things like apply. It's just like there's more future expected value of, you know, working on your email list

or on your website because otherwise it might be going away. So I think it's important to have a home base, but then also just like take advantage of everything else that's out there. So many of our customers grow massively for things like Facebook and advertising on and so on. These are amazing tools available to new businesses that, again, like 15 years ago, you would have to go to a television network and probably, I don't know, have dinners with decision makers and figure out how to raise a lot of money to place a lot of ads.

It's not just like, there was no possibility of just creating one ad or so. So it's very expensive. Now you can just like run a $100 campaign and see how it's going to go. So I think everything is just kind of ready and so much more accessible. Yeah, I would definitely agree with that. Are you seeing a spike at all in Shopify accounts opening? Usually during times, yeah, like it's, I don't have a right, I'm not right now seeing one, Like, it's generally, like, I mean, COVID was crazy and well-documented, and before, it's usually

then things get a little bit more tough going, but there's more entrepreneurship. In fact, it's funny, almost all the companies, this is something you can easily check with other people from tech industry and other industry, other entrepreneurs. If you ask them, almost all of them ended up starting their companies during some kind of nuclear winter or something, where, like, I showed before I started in the shadow of dot com. What was to remember that? That's a long time ago now.

But you know what dot com was? It's like mostly e-commerce. It's like pets.com and web then. And like, then it's just like, everyone's like, oh, never mind. All this technology stuff, all this e-commerce stuff is useless. Now it's all falling apart and we never need tech companies again. It turns out the ideas were right. They're just a bit too early.

Like there was not enough internet there. So, anyway, against this, I only learned really about this. I wasn't paying that much attention. Then I tried to fundraise, and then everyone told me, well, what, e-commerce? Like, haven't we tried this before? Yeah, yeah. What about, I mean, toughness in handling failure in entrepreneurship? I mean, do you have any failures at Shopify that you want to talk about how you can

got through them? I mean, I think the best I can do there is essentially just confirming that what much more eloquent guests you have will also say, I mean, I know you're like you have a jocco episode somewhere around here and like he, like, I think he makes a point really well. It's like you got a role with the punches. in fact, like, life is the school of hot knocks. It's like you've got to learn from this stuff.

Like a common sentence around Shaw before is like, well, if you have to eat shit, don't nibble. Like just go. I love that. I mean, I think that the, I've had a lot of failures. I mean, in, well, I can't say I look forward to the failures. because nobody does. I mean, it is your, to me, it's your roadmap. It's the, it's, all right, that happened, that sucked, that cost a lot of money, that costs a lot of time, that was painful, you know, whatever it is, but now you know, I'm never fucking going to do that again.

Exactly. Ever. Yeah. Maybe we have this case with like, I mean, we have had down times because someone made a avoidable mistake. And it's like, okay, well, what happens then? My sense is like anyone who has enough professional pride is plenty fine on the self-flagellations about this. Like, we don't have to add much. I'm just like, yes, this was expensive. Yes, we always shouldn't have happened.

see it as your tuition. It's like a degree, you know, one more thing that is going to be incredibly important for you to have learned for a rest of you. I know, like, people are like, well, are you firing people? Well, I mean, no, because I just paid a lot of money for them to learn this lesson. It's like this is the worst time to fire people about this. So I think, I believe in second chances. Now, if the same thing fails the same thing a bunch of times, then, you know, my offer of second chance

becomes highly conditional here but like it's like it's I think I don't know I've gotten to the point I'm feeling a little bit like a veteran of the roller course of entrepreneurship now then I find out my company is actually like I thought we were quoted something

and then I look deeper and I realize we're better at it I'm excited like it's like hey you're doing pretty okay and we were terrible at this thing, which we now know. So now I know exactly how to become a better company tomorrow. You know, just like, this is like, my road map is clear to your point, right? Like so, I think you can adjust to this, but almost, this is almost not helpful, I think, to say, because I don't think that makes it easier for people who have to go to hell. You just have to go for shit, like, eat some shit along the way.

You're going to make mistakes. I've made huge mistakes. I had to like an entire department, a massive part of a company with a thousand or a thousand people that we thought was going to be part of Shopify's what we call main quest, basically what we're working on in logistics. And we had to exit this business and I wrote about it publicly about how I made this decision. And because I also think you need to, you know, say when you make a mistake, it's okay to say it right like it's it's uh i think keeping the quorum there is just fake like it's just

like i've made reason why i make good decisions and have built good intuition is because i have added failure lessons more than most along the way at least in this space so is a husband and a father of three this is another this is another thing that i'm constantly battling about is, is, you know, how do you find the balance between, you know, work and family? Yeah. Balance is hard, right? Like, I think balance is, like, harmony, I guess, is better, I think. I like working.

I really just do like working a lot. I love my job. I love a puzzle that life drops on my desk every day. It's a different set of puzzles every day. day and I happen to like puzzles. I, um, you know, I do, if it's at all possible, like, I mean, I'm, we're having dinner together, right? Like, it's, my wife insists on dinner at 6 p.m., which I find inconveniently early as a European,

but like I've acclimatized. And we have dinner together and then, you know, my kids now, every boy is they're all sort of 10, it's like 11, 13, 15 now. So there's plenty of things for us to do together, which is really, really awesome. And, you know, we played video games together and stuff like. We try to have hobbies, but like I do, you know, I do try to be there as much as I can.

Luckily we have phones. I know phones have a bad rap. they're like people are not present, but like, thanks to the invention of phones, I had a much, much, much larger presence in my kid's life than I could have had if phones wouldn't have been invented. And so, you know, a little bit of multitasking, a little bit of, like, hey, I can actually go with you to the thing because in worst case, I need to step out and take a phone call. And the kids also knowing that, you know, that's a choice that I make and and I stand by and they will learn that.

Like, they can make different choices later, but like, we're building important companies that are meaningful, and that's what our family doors. We're builders, right? And so I think that's keeping all this in harmony, rather than trying to think about it as like rivalrous too much, has spoke very, very well for us. Are you able to be present with your family?

Yes. Or are you constantly thinking about how to improve and make Shopify more successful? Okay. That is a background process that can go on very low priority, but I don't think I can turn it off truly. I don't think I'm able to. It's just, so does that mean I'm not present? I mean, it's like, again, it's me. It's like as present as I can be, right? Like, am I as present with my family as I can project presence on any. individuals yes like absolutely but I don't know there's like I'm kind of I think by nature a little bit like predisposed for solving problems and wrestling with issues and like again I like puzzles so I think I don't know I've learned to be unapologetic about that because again a lot of books say

talk in absolutes. Now of books talk, you are absolutely present in a way that I don't even think is accessible to people of AED, frankly, or not. And somehow that is like you know, all

of the implied moral judgment of a book is now resting on your shoulders if you say no to this. And I was like, yeah, like, I don't know, I think I have a pretty good thing going and I have a deep and meaningful relationship with my kids. So so anyway, I think that's a goal.

Do you, are you teaching your kids entrepreneurship? Yeah. What, what age did you start? Like, as soon as I could talk. It's like, no, I, like, how would you improve anything around you? Like, how you would you redesign your toys if you were, if you have a question, I'll answer every question. I mean, I have policies, I should say this stuff. Like, so.

You asked them how they would redesign their toys? Oh, yeah. Oh, yeah. Like, they don't get an allowance, but they get to pay. but they get to pitch. So, like, they can look for opportunities, like, you know, wake beliefs or whatever, and we negotiate what they would make.

And, you know, the nice things they've all realized how lazy I am, so, or busy. And so, therefore, they, and they completely intuitively, by the time of, I think the youngest was for, worked out, how to make a cartel and like it's just like we're going through all of business history here

like they now have monopoly on all sorts of things and they're stocking my favorite chocolate that I have a weak spot for so like it's like it's hilarious and I love it. It's like I love them kind of hacking the system and just because again they are also little people

and every person is a intelligent actor in a local incentive system and for all the design of an incentive system you can have and do as a parent, you can't really prepare them. So, but you know what? They're pretty good at preparing themselves. They're pretty good to see through the games

and figure out what's behind it. And I just, I think I love all that. We've done lots and lots of, like, trying to expose them to hard problems. Like, that was really hard because of COVID the COVID period, and especially Canada COVID. especially Canada COVID was kind of COVID was sort of like California COVID. And a little bit more enthusiastic about somehow never going outside again than most places.

And so, so, you know, sort of the school of hard knocks was kind of hard to reproduce. So we did a lot of this with, you know, I just got them to play way too hard video games, like together as a team, you know, like and like basically inducing chaos and problem-solving and, you know, Dungeon and Dragons, my wife ran a Dungeon and Dragons campaign with them, which was, like, designed to be really hard. And so it's like this kind of stuff. So this is other things we prioritized and it had.

I love that, how would you reinvent your toys? I want to break the idea as early as possible with my kids that the world just is. Everything is changeable. Everything is improvable. Everything around them is designed by people who know more intelligent than they are, and potentially didn't even care about as much about the thing as they care right now as kids, because there's nothing more real than a kid's, a kid that's all in into something.

There's no, they don't do that for any kind of external or extrinsic approval. It's all intrinsic and true. and true. And the real motto of our family is really that it's a super simple sentence. It's just everything is interesting. And so we don't allow our kids to say things like that they're not good at something. They can only say they're not, they're not yet good at something. Like, they correct each other at this point.

It's like, I'm no good at public speaking. Everyone looks at them yet. And then everything's okay. The reason is, like, everything's interesting because it is. Like, people, I don't want my kids to treat anything as a black box, right? Like, this just is, like, a computer is not allowed to be a computer. Like a computer actually does things. It's a thing called a transistor which makes some sort of a transistor,

which makes something called a NAND gate, which then makes some other gates, and at some point you can do calculations, and then there's memory and accumulators in a CPU, and eventually, it just math. It doesn't do anything magical. It just does a sequence of steps that manipulate memory really, really fast,

and so magical things happens when you can do something very simple, very fast. And so, you know, just breaking black boxes with them, them is important. So my policy is when one of my kids comes up at a book from home anywhere and ask me a question, I will stop what I'm doing and I'll answer it always. And they know to not misuse that now, but they used to, which was also adorable and funny. And usually I try to answer their question. If I can't, I sit down with them and figure out with them how I would research the answer to the question now, and then I send them to go do it, and then they have to report back, ideally, usually at dinner.

And so, I think that was a little then yet and how this all goes, and I think that's, I mean, like, are we perfect parents? No one is, right? Like, this is for us. Yeah, you're instilling critical thinking into your kids. I love that. I just started this with my... up with my four-year-old. Now when he asked me for help, I ask him if he's looked for any other solutions. Exactly. Instead of helping him, he's four. I make him look for other solutions. And then sometimes he can find one. Sometimes he can't. But at least he's going through the motions of, oh, wait, maybe there's another way out of this. Maybe there's another way to solve this. Maybe there's another way to fix this instead of just asking for mom and dad to help every single time. I love that.

It's exactly the same thing. What I love specifically is the, like, the implication of everything is interesting is really, really helpful, right? Because, you know, like, I don't know. Kids have to learn things in school that they just don't find interesting initially. And it's like, or some concepts is like, okay. Okay, why. But it turns out the story behind this is always interesting.

I remember I read a book about the history of, I have no idea why I read this book, but it's a history of double entry accounting and why it got invented, what problem it solved. And it's a crazy story. It's like it was invented in Venice by the merchants and it's literally responsible for the nation empire. And it's like, holy shit, that's like double entry accounting. That sounds like worse than watching paint dry, right? Like, but it turns out that if you understand the story behind stuff, like why someone did a thing, or what problem it solved, or at least what the characters were like that had to solve a problem, everything is interesting. And

it's like just so like finding the interesting bit to connect with the thing that you want to understand, It's actually also a skill. And it's something I had to learn, right? Because I had to like, man, trust me, I love computers. I love engineering. I did not need to learn finance. Like, it wasn't my first, you know, like, kind of had to do it.

A property CEO, and also like just like a lot. There's a lot. The cool thing about the job is like it's super high expectations, right? Like in terms of the range, which is perfect because I like building range. But I had to learn how to trick myself into wanting to learn things, because as anyone with authority problems I can attest to, I cannot just go learn stuff because someone told me. I can only learn the solutions to problems I've had.

And so I need to go and figure out how to construct the problem environment for myself, or at least make it a story I want to explore deeper by tinkering with it or something. I had to like, you know. So, anyway, I've learned how to trick my own brain to do it. And it's been really important. And with a kids, it's just as fun. Love it.

Love that. I'm totally stealing, though. How would you reinvent your toys starting today? You're right for it. But, well, Toby, let's take a break. Gents, let's be real. Most skin care isn't made for us. And if you want to look a little younger,

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subscribe to the vigilance elite newsletter right now I talk about all the stuff that's going bad because I'm concerned and I'm foolish enough to think that maybe I can make a difference. But, you know, I think it's weird because the interview that's released in today, we talk about this exact same thing. But, you know, I think the biggest, you know, we've made a lot of impact, you know, through this show on the, on, for the country and in the world and whatever, you have, you know. but I think but the thing like the biggest impacts that we've made are are the guys like Justin Hughes who painted these paintings and and veterans which we're going to talk about it's it's in the outline but but people just people that are coming out that are trying to trying to build a business trying to you know bring their gift to the world and nobody's

giving them the fucking attention or the or the the the the you know just a little bit of an exposure just enough to like let them see the light yeah you know and and and i think that's the biggest impact that we've had in the show it's not about you know exposing corruption or stopping fucking funding for the any of that it is it's it's it's people that have been able to make a new life because we gave them the time of day totally i mean also don't get me wrong i'm like plenty of grateful for exposing the bullshit too. It's just like, we need, like, it's more automatically viral, right?

And so, like, if everyone starts, like, only exposing the stuff that's wrong, we actually forget what's going right. There's an effect, I don't know if you come across this, I think Derek Thompson wrote about it. I was not like Atlantic, but I saw it for the first time. I'm doing fine, but everyone else is fucked, in fact, if you come across this, like, I think it's like 80% of people think, like, self-described in the United States as, I'm doing okay, but I think like 80% of the people around me don't. And like, that can't be true. Like, so how does, has our perspective so skewed?

There's some countries where it's like 90%, like South Korea. 90%? 90% of people think. What do you think it is? I mean, I think it's self-indulgence and the inability to self-reflect, if that's what you think. But I think it's not, like, it's not as many people are doing, like, people are doing, some people are doing poorly 100%, but it's not 80% of everyone else, right?

This is the thing. It's like, it's like, there's fewer, like, in fact, in a lot of ways, it depends on how you look at things. Like, again, like, I don't know, it's just like, like, like, the, richest person on planet Earth 100 years ago could not have had a cell phone. In fact, there's a lot of things they couldn't have had, they couldn't, you know, just like, we've come pretty far and like things, I just, I just, I refuse to believe that everything is going down in the shitter, I think what has changed is for gaining all the information, like, we are just like, and we're kind of really prepared for it.

We're like moving, like, I think the next, net amount of bullshit on planet Earth has probably been reasonably static. And the amount normal people will encounter in their life has exponentially increased, and I think that's skewing people's mind. The problem is it might be self-reinforcing, because I think pessimism, taking pessimistic perspective just means people don't do things that they otherwise. like if you think you can succeed or like like again you need some optimism to like you can't start a company unless you are somewhat optimistic about the future right like you got you kind

of have to know that at least your own tomorrow is going to be better after you start this company but not to engage in doing something and so um yeah i i think if you're all like talk ourselves into everything is fucked around us then um i think then you know just we can talk ourselves into literally that happening, even though it's currently, at least by a survey, people would not self-described as being in bad shape. This is a good point. I mean, do you feel like that, do you consider yourself to be an optimist? Yeah. I mean, I'm medium-long-term, I'm long-term optimistic.

Short-term, I can be pessimistic, too. I mean, fundamentally, so there's a study of this. Matt Ridley, I wrote a great book called Rational Optimist. And he sort of made a study of optimists throughout time. And the conclusion of the book is everyone who made future predictions that they're optimistic was ridiculed, like underperformed the people who were naysayers about the future. Very much so. Got a lot of shit for it.

And all of them were too pessimistic for the future. the future that actually ended up happening on every issue they were optimistic about. So it's funny, we just have a bias towards the negative. And so, you know, I'm long-time optimistic, but I think the reason why we end up in for optimistic outcomes is because the high agency pessimists help us steer us around the problems. Right, so like the pessimists are really, really important as well. So, you know, I think this is how it composes. I mean, we talked about the AI earlier, it's clearly, I mean, from an individual perspective,

there's going to be a lot of disruption, but from a society perspective, there's just a lot to like that we might get to. And frankly, it's there anyway, so like even, like, this is not even like, you can't stop it. But like, I think there's a lot of people as talking about the negative downsides with all the clear and you know kind of amazing things that could happen and so i think that's it's worth keeping those in mind too the you know just i mean you live with this stuff i don't but i have interviewed a lot of tech giants this year you'd be one of them and you know you know what's

funny with the a i stuff is that all the people that don't understand anything about a i are the are the naysayers the pessimists and you know in i mean i have my own concerns You know, I'm not, I'm not saying that, you know, that I don't because I do, I have a lot of concerns about AI, but I don't understand it. But when I talk to people like you, like Sri Ham Kashan and anybody, Joe Lonsdale, Palmer Lucky, Trey Stevens, you know, all, anybody, Alex Wang, you know, all these guys that are, that are in it, that in tech, that understand it. Not one of them is wanting to pull the brains back on AI. Everyone's an optimist. And so when you think about it like that, it's like, well, everybody that actually knows what the fuck is going on is an optimist. And everybody that doesn't have a damn clue what the hell is going on, probably don't even use AI at all in their daily life,

are the ones that are pessimistic and saying that the world's coming to an end because of AI. In industry, it's a bit more of a mix. It's like there are some people who have been absolutely instrumental to the inventing AI who are quite on the other, like on a more pessimistic side there. But like, it's, like, I think what's, like, I think what the pessimists also just, like, they take a very reductionist view of humans. Like, humans are volumative, like, adaptable species. Right, we always talk, like, the joke around nuclear war has always been, it's just the cockroaches left, now it's the humans.

Like, we figure out everything. We are way more zillion. We live in a lot more crazy. I live in Ottawa, Canada for 20 years. That place is fucking cold. It's like, it's like, there's just, fucking no way anyone could survive at this place without a huge amount of modern technology. Like, we basically, a, you know, might as well be an outpost of moon like there in the winter. It's like, you know, just like you grew out like in 15 layers and whatever cheek might be exposed is like hurting. Like it's like it's crazy at the worst days. And yet we live there and it's a wonderful place to live outside of maybe those days. At some point one of my sons asked like,

Dad, why do we live where the air makes you hurt? Which I thought was a pretty well-put question. Anyway, so, you know, like, technology is all around us, and technology actually is there to make our lives better and make us be able to do more and, like, make the ambitious people be able to accomplish more or, in fact, inspire people to, like, reach higher. Like, I mean, I don't know. I was inspired by the technology I used to build Snow Devil.

Like, I used random Japanese programming language. It was, it's not the program language itself, which is, like, ultimately more amazing than other programming languages. These are all just sort of dialects of each other. But, like, somehow it spoke to me, or rather, I felt my brain spoke Ruby, and I just didn't know it.

I found, like, I could write better code. I was more inspired to sit down. And, like, there's just technology doing this to me. And I find, like, exactly the same thing with AI. It's just like, like, the unbridled fun you can have, just tinkering with it, just trying things. Like, there's a new model that came out this week. And it's just like, you know, you make, like, incredible infographics, like, or just, like,

I was reading a white paper on some rather dry stuff. And I just put the white paper into this new model and said, show. me what like an amazing professor would have at the end of a lecture on this topic on their whiteboard. And it just short made the whiteboard. And it was all like here the concepts and connecting and showing. And it was beautiful. And it's like so much easier for me to learn this way because I just like the visual

thing. I just could sort of think myself into a classroom with an eccentric but wonderful professor making like blackboard sketches about the topic. It just like make all much more sense. And like, that's crazy. That's coming from a bunch of floating points that someone trained in a data center, not far from here. How is this possible?

This is like modern magic. And so it's like the wonder of it. It's just wonderful. And so I want to be optimistic because what happens is when more people, like I am not an artist. I can't even with an actual whiteboard, like after I know the topic perfectly ever make such a beautiful, like if any amount of time I could I could not have done the same thing and but I have

demand for this like I want like the computer do this for me now I know I can cause a computer to do this maybe there's a business there like if maybe you can follow this thought all the way to like a new form of education which then inspires more people and so on so on like this what we need to do is make services and products for each other, right? And that depends on the tools we get to use, and

those are giving us leverage, just like electricity did at Industrial Revolution. And so I just feel like it is quite predictable because we have played out this movie many times before in human history of what

happens when you give everyone an incredibly powerful new lever and tool. I'm with you. You know, I've If, I don't, I don't use it that much, but, you know, my, my, my, my, my, my, my team here, they, they use it every day. They're always wrapped up in it. They're always talking about it. You know, and you know what I've noticed is that it seems to, it, it's like you can offload bandwidth out of your mind into an AI. And it, it, it just frees up bandwidth. to make it, it enables you to work on, you know, more important things, more innovative things because the AI, you basically said this at the beginning of the interview at some point. Yes. That, you know, it's, at least I think you did, maybe in different words, but it's creating

more bandwidth in people's minds who learn how to use it. Yes. And, and I, I 100% see it in my team here. And so everything that I've actually seen, other than deep fakes is positive. Yeah. You know, and those are fraudulent, so they are illegal, right? Like this is the other thing.

Everyone's like, well, what we do about the things that can now be done? Well, they are legal. You know, like our existing body of laws is pretty clear on how we think about fraud, right? So, I mean, but like it's not, like, again, it, now I feel the need as everyone who talks about this to, acknowledge that they are, you know, anything that's powerful can be used powerfully for good and for bad. What then matters is how distributed it is. And I think it's also that we live in a time where like, I don't know, like the second,

like, again, I run a company that's like billions of dollars of, like, of revenue and is worth hundreds of billions of dollars. It's, I am in WhatsApp with the people running and training these models at all the labs because I am of the industry and I know them. I have no access to better models than everyone, right? Like it's the second they release something, it's going into an API. That API can be called from everyone's computer that is connected on the Internet, which really is every computer with the right command.

that you can literally copy from a website and paste into a window of a program you've never launched called Terminal. And it will respond from that quality API for less than a penny. And it's awesome that we live in a world where, like, we could live in an alternative world where these things are trained and someone pays $100 billion to purchase it. And then there's one of one and only one entity. or one company could use this and we are not living in that world. And I think that's amazing.

The open nature and the direct distribution in me is the thing that I'm so thankful for because it's completely path-dependent. This just happened. This is how the first one got released. It created an aesthetic for releasing these, and therefore all of them are released. We'll never think about it again. But the world is incredibly path-dependent. slightly different choices when the first chat GPT or GPT would have been released by a handful

of people in an office in San Francisco would have created a different go-to-market strategy, which then everyone would have copied that, and we would be in a completely different world. So I think we are one of the most optimistic outcomes there, like, these things are extremely well distributed and available, and everyone can tinker with them, and I think that's good. And you got a great way of thinking about things. I love chatting with you about all these random things. You know, we're getting a little, let's get into some of your hobbies. You know, on the break, by the way, nice shooting.

Thank you. That was amazing. I still smiling from that. I mean, this is me smiling. This is about how much you can. That was, like, God damn it. It's like, kind of hoped it wasn't as fun as. it wasn't as fun as it was because I have to go back to Canada and I can't do this so

it's a good time well I got you I got you a present so I don't know how you're going to get this back to Canada oh but if you can find a way that is uh go ahead open it up yeah that's this the SIG P-211 GTO SIG sours first attempt attempt at the 2011. That's the same one you were shooting out there. So I got a friend at Sig. His name's Jason. He's a huge fan of Shopify too. And anyways, he wanted me to present that with you. So I'm going to connect to you guys after the podcast. Thank you so much. That's crazy. And we will find a way. We will find a way. We will find a way. That's amazing. Yeah. I mean, I, like I told you, I actually, again,

I grew up in Germany and then lived in Canada. It's not, let's share the liberal laws related to weaponry. And so I just haven't, like, encountered. I'm just like actually, I know this sounds really basic to you, but like, they're beautiful. Like, the objects are, like, incredible. And anyway, it was so much fun. Thank you so much.

Maybe a new hobby for you. If you have to spend more time in the United States, it seems. Thank you so much. Okay. I have something which I think you will find cool too for you. Let me do it. This is amazing, thank you. And all right, so one of my favorite things we do

at shop, if I just started this like two years ago or so, maybe a bit more. Yeah, when you're building online business, it just feels like, sorry, it feels like not, it's a bit abstract, right? It's a bit abstract, right? Like, it's just like, it's not tantam. Like, if you're in a real store, in a real space like this, it's so tactile, it's like you can all take it in.

If it's busy, you see, you can sort of, so you build an online business and it's like, it's amazing, it can be very big, but like it's, there's something about our brain that cannot, even when you just look at numbers, it doesn't matter. So we were talking about, your business and like it's going really well. Like it's not just a little bit, like you started 10 years ago and like we've started making these like physical, just like moments to celebrate like milestones for people.

And then Harley, I was my president of Shopify, we take them and sometimes when we travel you get to give them to merchants as a, you know, appreciates. for doing business with us and celebrating a milestone. So they checked, you're not exactly where, but I feel like you like pressure. So I'm jumping with gun, so we have this award, which you will... Oh man, grow into... Oh, dude. That is awesome.

Congratulations, Sean Morin Show on reaching 100,000 orders. In January. 2026. So we must be close. You're close. This is awesome. We've used AI and predictive models to model this, and we believe we can just make it.

And I feel like you're, listeners can help out. And we'll get some good sales going and then you hit with 100,000 orders and then you have a new perfect artifact here for, you know, to celebrate this. This is awesome. Thank you. This is going in the studio.

And now we have to hit it. You have to hit it. And then I have one more thing which I'll show you. This is actually really cool. you were just about to say we were talking about hobbies. Have you seen, do you know what an LMP2 car is? No.

Okay, so L'Amour prototype. This is what I'm racing in South Ever Tech. So this is what the car looks like. This is the next, this is just the way the design looks. Yeah, I'm really excited. You know, cars are faster than they look cool, right? so and that is cool

and on that card you have like we have a space reserve for shoprifying merchants so uh yeah like pretty your brand like dude what like yeah

vigilance leads holy shit this is awesome are you serious let's go it's cool we we love uh

uh reping our our brands So... Dude. Thank you. Holy shit, that's cool. Yeah. Thank you.

If you come to one of our races, they are really fun. I would love to come to one. Are you going to race? Yeah. It's... Yes. So fun. It's every single time I get into these cars, I'm like, I can't believe they let me do this.

And then for a first lap, I'm like, I can't believe, like, how is this supposed to work? supposed to work and then you just get used to it and you remember it and then it goes good but man um thank you that is very cool thank you i think that's very cool thank you and thank you so much for a kind gift that's awesome my pleasure so let's move into i mean you have some extreme hobbies calculated risks let's talk about some of that okay so i don't look i feel extremely I've conscious to talk to you about risk. I feel like, I don't, that's not, maybe a little bit more on an adrenaline side.

Let's put it like this. But, yeah, I mean, I like kiteboarding. That's fun. But, like, I think, like, motorsport is like, you know, just something I got into the last 10 years and I have started taking much more seriously now. As every hobby, it's full of terms and lingo and so on. It's hard to talk about it without falling into terms that people have no idea about.

But I love, I mean, the first time I got on a track, I was just like, it was kind of similar to the shooting earlier. It's like, I thought I'm going to like it, but of course it was so much better than like it expected, God damn it. And so, unfortunately, I know this movie. Anyway, and so, you know, I kept coming back to track and track days. And eventually, I did some races with friends, you know, like, in like, Masa Miadas, right? Like, you're just like, all beaten up Massa Miads, like, rip out everything, make them light. And we did endurance racing, which I like particularly.

It's like when you go and race with some... other people, like some other drivers together for, you know, six, eight hours and you share the car. I didn't take it initially too seriously and just had fun. I just, I mean, my common story for me has always been, like, I love doing difficult things surrounded by friends. And to me, entrepreneurship is like this, you know, just like racing with teammates is really good. And, yeah, eventually I get in a car that is called a, like, a radical car, so I've got a track.

Like a car that's like, it doesn't look like a, I don't know, McLaren or a Ferry or something. It's just made for the track. It has, like, lots of downforce, right? Downforce, I mean, as in, like, pushes the car to have extra grip, the faster it goes. It's, you hear these stories about Formula One cars who can, could drive on the ceiling of a tunnel. No problem. Because I can, it's like they generate a ton of downforce. Anyway, so I got into this and that became my hobby.

And the best thing about it is that it's something, it's one of the only things that you can do with professionals together. It's like amateur and professionals drive in endurance racing together. And so yeah, I'm racing cars that are these high-down-force cars, they call Lamar prototypes, LMPs, LMP2s, to be specific,

which is the top class of amateur, like pro-M amateur class as an amateur. And yeah, Daytona 24 hours is the biggest race I've done. I am planning to do the

24 hours of Lamar this year, which is the largest race in the world. That's awesome. And I just love it. That's awesome. I mean, it seems like you talk a lot of, you talk a lot about risk, calculated risk. It's in, I mean, it's in the, it's in, it's in my outline several different times. I mean, what do you say to people that go through life, always playing it's safe? Yeah. curious what you're what do you do because it seems like

for I've had this observation like I can usually tell who of the people I know like broke a bone as kid you know just because if they didn't

they just spent a lot of their life trying to avoid to ever break a bone and the ones who did kind of know that it's kind of it sucks but it's not that big of a deal and I think ultimately it's better

to break your bow at some point as a kid when you heal pretty quickly and then afterwards I think

people make too much of risk I think I mean it's clearly an factor but like to avoid risk you have to be

careful but if careful I don't know it's better to be competent than careful just like get good at things like that are worth doing and then like figure out how to get

there and just just do it's like it's I don't know I there's so much like the total possibility of a total possibility space for a company of moves that are good or ideal that better don't also have a good deal of risk if that's that's a good the only space you can operate on in a company, there's no chance you're going to make it compared to someone else in the same space that will take some risks. The problem is you just, you will obviously look foolish at times, like you take risk, it's against public, you will have to accept something doesn't work, and they do, and you move on, and you do that once or twice, and then you realize, well, that's not so bad.

just like we're breaking the bones, and then you have so many more possibilities in front of you. And so with hobbies, it's kind of the same. Just have to take some risks, and I like adrenaline, and so I suppose it helps me. I call all racing Zen Buddhism at 300 kilometers an hour, or whatever, 200 miles, I suppose, almost. It grounds me and I can focus. Well, Toby, we're wrapping up the interview. I know you got a flight to catch, so I just have a couple of questions left. One of them being for future entrepreneurs, for people that are on the edge right now, wanted

to quit their job, one to take a stab entrepreneurship, find their freedom. I mean, what advice do you have for new entrepreneurs coming into 2026? I think the most important sentence that everyone can internalize is you can just do things. I love that sentence. I love that that's a meme. That's a kind of sense that is whispered amongst entrepreneurs and entrepreneur get-togethers in the past and now it's like trending on social media.

And I think this is one of the best things that can possibly happen. Just honestly, like reps, I was talking with, a while ago with like one of our customers, entrepreneurs is a comic called Jim Shark, which I think a lot of people have heard about. And, like, Ben, the founder of Jim Shark did five other stores before Jim Shark. And he was delivering Domino's pizzas the entire time, and Jim Shack just hit, right? And like, do the reps, like, just try it. The thing that people need to understand about entrepreneurship is, like, the failure case is not failure.

The failure case is not learning anything. And I think it's much more risky to not try, like, building a business from that perspective. Everything you do, everything you learn, every skill you pick up a longer way is going to be the few years forever. And the experience you do, even if the thing doesn't automatically plan out, is something that you're going to bring to literally every task you'll ever do. This is a wonderful thing about, is our intuition is underrated, our intuition is our entire past, all our life's experience rolled out for us, brought to the moment to try to make the best possible choice for the conundrum in front of us.

And if that involves what it's like to start something, to build something, to negotiate deals, to potentially have employees, to be responsible for someone's livelihood. If any of those things are in your past, you just will make a lot of quite valuable decisions with more accuracy afterwards and higher competency. And so I think it's incredibly valuable as a pursuit. And what do you know, it might actually work. You know, it just turns out that unless you're trying to build a business that is sort of another version of something that someone else has already done without many modifications,

if that's what you're doing, that's pretty busy space. But again, on the internet you need to find you 1,000 true fans. That's it. That's the job. If you build something that a thousand people will be deeply into, you'll figure out how to build this as a sustainable business afterwards. And that's much easier to do when you build something that you yourself are incredibly excited about than if you go and build something that other people might deem to be a good market for you to go into.

And I've seen this over and over and over again, that the best businesses on the system and in general in the world are things that solve problems that the entrepreneurs with, you know, just like they spoke to them. They found, like, there needs to be founder product fit, more than there needs to be product market fit. I think founder product fit is actually one of those things which I think is often overlooked. And I mean, I'm obviously incredible privilege and lucky here because I found it very, very early. Again, you find your gift, hopefully, if you're so lucky. You then develop your gift and cultivate the skill set, as I did with programming, and then you end with building commerce software, and then you figure out a path to giving it away,

which if then other people deem that of value and pay for it, which, again, is one of the most sincere ways of appreciation and a vote for everything you've built. If that all comes together, you have a business that can sustain you, and then you can see where it goes, and some of these journeys just go pretty far and, you know, or, in fact, never end, which is the best, like, the best thing to encounter is one of those problems that you deeply care about, trying to solve it, but you can't. because it's like infinite and we just like get to keep doing it.

And that's, I think that's really amazing when it happens. And all of us is locked away behind entrepreneurship. So it's best to just get the reps. Yeah. Man, you are just, you need to get out there more. I mean, I think you're helping me with that right now. You're extremely motivating. And I mean, it didn't.

You're kind of, kind of say. bet i'm not just saying that i mean i'm i'm i'm the motivation that you can bring towards future entrepreneurs is massive and um and i'm huge on entrepreneurship i hope all i hope all my kids are entrepreneurs like i never want them to have to fucking work for somebody and um and i'm just you know we're i don't even know if that was in the episode or out of the episode but you know i mean i told you that you know the the number one thing that i get out of this and i think that the biggest impact i can make is on future entrepreneurs and uh and i just fucking love doing it man it's just to be able to make somebody self-sufficient and just find the freedom of entrepreneurship and in all the

things that come with it and you know i am a pessimist i will bitch i will i will bitch with the best of them but you know and all on like there's fucking nothing that i would rather be doing and i bitch because i'm passionate about what i'm doing they're helping get to the port optimistic outcomes. You know what's the craziest, I need to say this because I just like, you will appreciate this. Like, there's like, again, public company, you can put everything in a spreadsheet and it's just like reduces the fidelity of a world thing.

You know, the stat that like be at Shopify, or certainly I at Shopify, like separate more than any other. It's like every 24 seconds someone has a first sale. Man, that's cool. every 24 seconds somebody has their first sale that is awesome it's a great feeling it's great feeling because it's like I mean this is like it it's it's it's awesome to have a personal mission it's it's awesome to have like like trying like again I just like you care about entrepreneurship a great deal and like being able to build something that

then causes more of it is like incredibly gratifying but that scale is just wonderful and it just means like there's just so much demand and like again we can make it simpler and just like it's it's like such a good moment right now but yeah like you know every 24 seconds there's a chance that this is someone else's someone's first sale and they will remember that for the entire life and um again their identity might change in that moment from being a builder to now being an entrepreneur that someone else has deemed valuable, like deemed or anointed to be a true entrepreneur

by purchasing, making my initial purchase. And yeah, that's what it's all about, isn't it? That's what it's all about. Well, Toby, it was an honor to get to know you, to interview you, to bring your story, and just pick your brain, and to listen to some of that knowledge. And I hope to see again. And I love, love, love what you're doing for entrepreneurs.

So thank you. Awesome. Thank you. I enjoyed it was a great deal. This was fantastic. Thank you so much for having you. No matter of you. No matter where you're watching Sean Ryan's show from, if you get anything out of this,

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